peer reviewed research papers 21 26 249 - …glyco/research/peer reviewed... · 15. bundle, d.r....

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PEER REVIEWED RESEARCH PAPERS 1. Bundle, D.R. and Shaw, N. Synthesis of 2-acetamido-6-O-(2-acetamido-2-deoxy-ß-D- glucopyranosyl)-2-deoxy-D-glucopyranose. Carbohydr. Res., 21, 211-217, 1972. 2. Bundle, D.R., Jennings, H.J. and Kenny, C.P. An improved procedure for the isolation of meningococcal, polysaccharide antigens, and the structural determination of the antigen from serogroup X. Carbohydr. Res., 26, 268-270, 1973. 3. Bundle, D.R., Jennings, H.J. and Smith, I.C.P. The carbon-13 nuclear magnetic resonance spectra of 2-acetamido-2-deoxy-D-hexoses and some specifically deuterated, O-acetylated, and phosphorylated derivatives. Can. J. Chem., 51, 3812-3819, 1973. 4. Bundle, D.R., Smith I.C.P. and Jennings, H.J. Determination of the structure and conformation of bacterial polysaccharides by carbon-13 nuclear magnetic resonance. J. Biol. Chem., 249, 2275-2281, 1974. 5. Bundle, D.R., Jennings, H.J. and Kenny, C.P. Studies on the group-specific polysaccharide of Neisseria meningitidis serogroup X and an improved procedure for its isolation. J. Biol. Chem., 249, 4797-4801, 1974. 6. Bundle, D.R. and Jennings, H.J. The synthesis of 2-acetamido-2-deoxy--D-glucopyranose 4- phosphate. Can. J. Biochem., 52, 723-725, 1974. 7. Lemieux, R.U., Bundle, D.R. and Baker, D.A. The properties of a synthetic antigen related to the human blood group Lewis-a. J. Am. Chem. Soc., 97, 4076-4083, 1975. 8. Lemieux, R.U., Baker, D.A. and Bundle, D.R. A methodology for the production of carbohydrate-specific antibody. Can. J. Biochem., 55, 507-512, 1977. 9. Jennings, H.J., Bhattacharjee, A.K., Bundle, D.R., Kenny, C.P., Martin, A. and Smith, I.C.P. Structures of the capsular polysaccharides of Neisseria meningitidis as determined by C-13 nuclear magnetic resonance spectroscopy. J. Infectious Diseases, 136, S78-S83, 1977. 10. Lemieux, R.U., Boullanger, P.A., Bundle, D.R., Baker, D.A. and Venot, A. Binding studies of -D-galactopyranosyl antibodies. Intramolecular hydrogen bonding effects. Nouveau. J. Chimie, 2, 321-329, 1978 11. Bundle, D.R. and Josephson, S. A facile synthesis of methyl 3,6-dideoxy-L-xylo- hexopyranoside (colitose). Can. J. Chem., 56, 2686-2690, 1978. 12. Birnbaum, G.I. and Bundle, D.R. Solution conformation and crystal structure of methyl 3,6- dideoxy--D-ribo-hexopyranoside, an immunodominant sugar of O-antigens. Biochim. Biophys. Acta, 582, 515-524, 1979. 13. Bundle, D.R. and Josephson, S. Artificial carbohydrate antigen: Synthesis of rhamnose disaccharides common to Shigella flexneri O-antigen determinants. Can. J. Chem., 57, 662-668, 1979. 14. Bundle, D.R. and Josephson, S. Artificial carbohydrate antigens: The synthesis and conformation of a Shigella flexneri trisaccharide hapten. J. Chem. Soc., Perkin I, 2736-2739, 1979.

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Page 1: PEER REVIEWED RESEARCH PAPERS 21 26 249 - …glyco/research/PEER REVIEWED... · 15. Bundle, D.R. Displacement of sugar chlorosulphates by bromide, azide and acetate; a facile synthesis

PEER REVIEWED RESEARCH PAPERS

1. Bundle, D.R. and Shaw, N. Synthesis of 2-acetamido-6-O-(2-acetamido-2-deoxy-ß-D-

glucopyranosyl)-2-deoxy-D-glucopyranose. Carbohydr. Res., 21, 211-217, 1972.

2. Bundle, D.R., Jennings, H.J. and Kenny, C.P. An improved procedure for the isolation of

meningococcal, polysaccharide antigens, and the structural determination of the antigen from

serogroup X. Carbohydr. Res., 26, 268-270, 1973.

3. Bundle, D.R., Jennings, H.J. and Smith, I.C.P. The carbon-13 nuclear magnetic resonance

spectra of 2-acetamido-2-deoxy-D-hexoses and some specifically deuterated, O-acetylated, and

phosphorylated derivatives. Can. J. Chem., 51, 3812-3819, 1973.

4. Bundle, D.R., Smith I.C.P. and Jennings, H.J. Determination of the structure and conformation

of bacterial polysaccharides by carbon-13 nuclear magnetic resonance. J. Biol. Chem., 249,

2275-2281, 1974.

5. Bundle, D.R., Jennings, H.J. and Kenny, C.P. Studies on the group-specific polysaccharide of

Neisseria meningitidis serogroup X and an improved procedure for its isolation. J. Biol. Chem.,

249, 4797-4801, 1974.

6. Bundle, D.R. and Jennings, H.J. The synthesis of 2-acetamido-2-deoxy--D-glucopyranose 4-

phosphate. Can. J. Biochem., 52, 723-725, 1974.

7. Lemieux, R.U., Bundle, D.R. and Baker, D.A. The properties of a synthetic antigen related to

the human blood group Lewis-a. J. Am. Chem. Soc., 97, 4076-4083, 1975.

8. Lemieux, R.U., Baker, D.A. and Bundle, D.R. A methodology for the production of

carbohydrate-specific antibody. Can. J. Biochem., 55, 507-512, 1977.

9. Jennings, H.J., Bhattacharjee, A.K., Bundle, D.R., Kenny, C.P., Martin, A. and Smith, I.C.P.

Structures of the capsular polysaccharides of Neisseria meningitidis as determined by C-13

nuclear magnetic resonance spectroscopy. J. Infectious Diseases, 136, S78-S83, 1977.

10. Lemieux, R.U., Boullanger, P.A., Bundle, D.R., Baker, D.A. and Venot, A. Binding studies of

-D-galactopyranosyl antibodies. Intramolecular hydrogen bonding effects. Nouveau. J. Chimie,

2, 321-329, 1978

11. Bundle, D.R. and Josephson, S. A facile synthesis of methyl 3,6-dideoxy-L-xylo-

hexopyranoside (colitose). Can. J. Chem., 56, 2686-2690, 1978.

12. Birnbaum, G.I. and Bundle, D.R. Solution conformation and crystal structure of methyl 3,6-

dideoxy--D-ribo-hexopyranoside, an immunodominant sugar of O-antigens. Biochim. Biophys.

Acta, 582, 515-524, 1979.

13. Bundle, D.R. and Josephson, S. Artificial carbohydrate antigen: Synthesis of rhamnose

disaccharides common to Shigella flexneri O-antigen determinants. Can. J. Chem., 57, 662-668,

1979.

14. Bundle, D.R. and Josephson, S. Artificial carbohydrate antigens: The synthesis and

conformation of a Shigella flexneri trisaccharide hapten. J. Chem. Soc., Perkin I, 2736-2739,

1979.

Page 2: PEER REVIEWED RESEARCH PAPERS 21 26 249 - …glyco/research/PEER REVIEWED... · 15. Bundle, D.R. Displacement of sugar chlorosulphates by bromide, azide and acetate; a facile synthesis

15. Bundle, D.R. Displacement of sugar chlorosulphates by bromide, azide and acetate; a facile

synthesis of methyl, 3,6-dideoxy--D-ribo-hexopyranoside. J. Chem. Soc., Perkin I, 2751-2755,

1979.

16. Bundle, D.R. Antibody to an artificial disaccharide antigen cross-reactive with Neisseria

gonorrhoeae lipopolysaccharide. Can. J. Biochem., 57, 367-371, 1979.

17. Banoub, J. and Bundle, D.R. Stannic tetrachloride catalyzed glycosylation of 8-ethoxy-

carbonyloctanol by cellobiose, lactose and maltose octaacetates; synthesis of and glycosidic

linkages. Can. J. Chem., 57, 2085-2090, 1979.

18. Banoub, J. and Bundle, D.R. 1,2-orthoacetate intermediates in silver trifluoro-

methanesulphonate promoted Koenigs-Knorr synthesis of disaccharide glycosides. Can. J.

Chem., 57, 2091-2097, 1979.

19. Unemura, J., Birnbaum, G.I., Bundle, D.R., Murphy, W.F., Bernstein, H.J. and Mantsch, H.H.

The correlation between O-H stretching frequencies and hydrogen bond distances in a crystalline

sugar monohydrate. Can. J. Chem., 57, 2640-2645, 1979.

20. Josephson, S. and Bundle, D.R. Artificial carbohydrate antigens: The synthesis of the

tetrasaccharide repeating unit of Shigella flexneri O-antigen. Can. J. Chem., 57, 3073-3079,

1979.

21. Bundle, D.R. and Josephson, S. Artificial carbohydrate antigens: The synthesis of tetra-

saccharide hapten, a Shigella flexneri O-antigen repeating unit. Carbohydr. Res., 80, 75-85,

1980.

22. Josephson, S. and Bundle, D.R. Artificial carbohydrate antigens: The synthesis of rhamnose

trisaccharide and disaccharide haptens common to Shigella flexneri O-antigens. J. Chem. Soc.,

Perkin I. 297-301, 1980.

23. Iversen, T. and Bundle, D.R. A new and efficient synthesis of β-L-rhamnopyranosides.

Carbohydr. Res., 84, C13-C15, 1980.

24. Bundle, D.R. and Josephson, S. Chlorosulphation of amino sugars: Synthesis of methyl 2-

acetamido-4-amino-2,4,6-trideoxy--D-glucopyranoside (bacillosamine) from a D-glucosamine

derivative. Can. J. Chem., 58, 2679-2685, 1980.

25. Iversen, T., Josephson, S. and Bundle, D.R. The synthesis of streptococcal groups A, C and

variant-A antigenic determinants. J. Chem. Soc, Perkin I. 2379-2385, 1981.

26. Iversen, T. and Bundle, D.R. Benzyl trichloroacetimidate, a versatile reagent for acid-catalyzed

benzylation of hydroxy-groups. Chem. Comm., 1240-1241, 1981.

27. Iversen, T. and Bundle. D.R. A direct and efficient synthesis of β-L-rhamnopyranosides. J. Org.

Chem., 46, 5389-5393, 1981.

28. Neurohr, K.J., Mantsch, H.H., Young, N.M. and Bundle, D.R. Carbon-13 nuclear magnetic

resonance studies on lectin-carbohydrate interactions: Binding of specifically 13C-labeled

methyl -D-lactoside to peanut agglutinin. Biochemistry, 21, 498-503, 1982.

29. Perry, M.B., Bundle, D.R. Daoust, V. and Carlo D.J. The specific capsular polysaccharide of

Streptococcus pneumoniae type 15F. Mol. Immunol., 19, 235-246, 1982.

30. Bock, K., Josephson, S. and Bundle, D.R. Lipopolysaccharide solution conformation: Antigen

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shape inferred from high resolution 1H and 13C nuclear magnetic resonance spectroscopy and

hard-sphere calculations. J. Chem. Soc., Perkin II, 59-70, 1982.

31. Iversen, T. and Bundle, D.R. Antigenic Determinants of Salmonella A and D1 synthesis of

trisaccharide glycosides for use as artificial antigens. Carbohydr. Res., 103, 29-40, 1982.

32. Iversen, T. and Bundle, D.R. Synthesis of the colitose determinant of Escherichia coli 0111 and

3,6-di-O-(-D-galactopyranosyl)--D-glucopyranoside. Can. J. Chem., 60, 299-303, 1982.

33. Neurohr, K.J., Bundle, D.R., Young, N.M. and Mantsch, H.H. Binding of disaccharides by

peanut agglutinin as studied by ultraviolet difference spectroscopy. Eur. J. Biochem., 123, 305-

310, 1982.

34. Bundle, D.R., Gidney, M.A.J., Kassam, N. and Rahman, A.F.R. Hybridomas specific for

carbohydrates; synthetic human blood-group antigens for the production, selection and

characterization of monoclonal typing reagents. J. Immunol., 129, 678-682, 1982.

35. Bhattacharjee, A.K., Bennett, J.E., Bundle, D.R. and Glaudemans, C.P.J. Anticryptococcal type

D antibodies raised in rabbits. Mol. Immunol., 20, 351-359, 1983.

36. Kenne, L., Lindberg, B., Soderholm, E., Bundle, D.R. and Griffith, D.W. Structural studies of

the O-antigens from Salmonella greenside and Salmonella adelaide. Carbohydr. Res., 111, 289-

296, 1983.

37. Pinto, B.M. and Bundle, D.R. Preparation of glycoconjugates for use as artificial antigens: A

simplified procedure. Carbohydr. Res., 124, 313-318, 1983.

38. Wessel, H.P. and Bundle, D.R. Artificial carbohydrate antigens: A block synthesis of a linear

tetrasaccharide repeating unit of the Shigella flexneri variant Y polysaccharide. Carbohydr. Res.,

124, 301-311, 1983.

39. Wessel, H.P., Iversen, T. and Bundle, D.R. Synthesis of the trisaccharide moiety of

gangliotriosylceramide, Asialo GM2. Carbohydr. Res., 130, 5-21, 1984.

40. Caroff, M., Bundle, D. R. and Perry, M. B. Structure of the O-chain of the phenol-phase soluble

cellular lipopolysaccharide of Yersinia enterocolitica serotype O:9. Eur. J. Biochem., 139, 195-

200, 1984.

41. Shearman, P.J., Bundle, D.R., Romanowska, E., Lugowski, C. and Bogulska, M.

Characterization of anti-Citrobacter 036-specific polysaccharide monoclonal antibodies. Can. J.

Microbiol., 30, 91-97, 1984.

42. Carlin, N. I. A., Lindberg, A. A., Bock, K. and Bundle, D. R. The Shigella flexneri O-antigenic

polysaccharide chain: Nature of the biological repeating unit. Eur. J. Biochem., 139, 189-194,

1984.

43. Bock, K., Meldal, M., Bundle, D.R., Iversen, T., Garegg, P.J., Norberg, T., Lindberg, A.A. and

Svenson, S.B. The conformation of Salmonella O-antigenic polysaccharide chains of serogroups

A, B and D1 predicted by semi-empirical hard sphere (HSEA) calculations. Carbohydr. Res.,

130, 23-34, 1984.

44. Bock, K., Meldal, M., Bundle, D.R., Iversen, T., Pinto, B.M., Garegg, P.J., Kvanström, I., Norberg, T., Lindberg, A.A. and Svenson, S.B. The conformation of Salmonella O-antigenic oligosaccharides of serogroups A, B and D1 inferred from 1H and 13C nuclear magnetic

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resonance spectroscopy. Carbohydr. Res., 130, 35-53, 1984.

45. Caroff, M., Bundle, D.R., Perry, M.B., Cherwonogrodsky, J.W. and Duncan, J.R. Antigenic S-

type lipopolysaccharide of Brucella abortus 1119-3. Infect. Immun., 46, 384-388, 1984.

46. Bundle, D.R., Gidney, M.A.J., Perry, M.B., Duncan, J.R. and Cherwonogrodzky, J.W.

Serological confirmation of Brucella abortus and Yersinia enterocolitica O:9 O-antigens by

monoclonal antibodies. Infect. Immun., 46, 389-393, 1984.

47. Pinto, B.M. and Bundle, D.R. Antigenic determinant of Salmonella serogroup B. Synthesis of a

trisaccharide glycoside for use as an artificial antigen. Carbohydr. Res., 133, 333-338, 1984.

48. Birnbaum, G.I. and Bundle, D.R. Conformation of methyl 3,6-dideoxy--D-arabino-hexopyranoside, the immunodominant sugar of Salmonella serogroup D1: Crystal structure, 1H NMR analysis and semi-empirical calculations. Can. J. Chem., 63, 739-744, 1985.

49. Gidney, M.A.J., Bundle, D.R., Godard, A. and Griffiths, B.W. Development and

characterization of monoclonal antibodies to pregnancy-specific 1-glycoprotein. Can. J.

Biochem., 63, 737-742, 1985.

50. Wessel, H.P., Iversen, T. and Bundle, D.R. Acid-catalyzed benzylation and allylation by alkyl

trichloroacetimidates. J. Chem. Soc., Perkin I, 2247-2250, 1985.

51. Wessel, H.P. and Bundle, D.R. Strategies for the synthesis of branched oligosaccharides of the

Shigella flexneri 5a, 5b and variant X serogroups employing a multifunctional rhamnose

precursor. J. Chem. Soc., Perkin I, 2251-2260, 1985.

52. Emmrich, F., Bundle, D.R., van der Zee, J., Out, T., Zenke, G. and Eichmann, K. Two human

IgM myeloma proteins with unusual specificities for streptococcal carbohydrate-associated

epitopes. Scand. J. Immunol., 21, 119-126, 1985.

53. Lemieux, R.U., Venot, A.P., Spohr, U., Bird, P., Mandal, G., Morishima, N., Hindsgaul, O. and

Bundle, D.R. Molecular recognition. V. The binding of the B human blood group determinant

by hybridoma monoclonal antibodies. Can. J. Chem., 63, 2664-2668, 1985.

54. Bundle, D.R., Gerken, M. and Perry, M.B. Two dimensional NMR at 500 MHz: The structural

elucidation of a Salmonella serogroup N polysaccharide antigen. Can. J. Chem., 64, 255-264,

1986.

55. Perry, M.B., Bundle, D.R., MacLean, L., Perry, J.A. and Griffith, D.W. The structure of the

antigenic lipopolysaccharide O-chains produced by Salmonella urbana and Salmonella

godesberg. Carbohydr. Res., 156, 107-122, 1986.

56. Carlin, N.I.A., Gidney, M.A.J., Lindberg, A.A. and Bundle, D.R. Characterization of Shigella

flexneri specific murine monoclonal antibodies by chemically defined glycoconjugates. J.

Immunol., 137, 2361-2366, 1986.

57. Pinto, B.M., Morrisette, D.G. and Bundle, D.R. Synthesis of oligosaccharides corresponding to

biological repeating units of Shigella flexneri Y polysaccharide. Part 1. Overall strategy,

synthesis of a key trisaccharide intermediate, and synthesis of a pentasaccharide. J. Chem. Soc.

Perkin I, 9-14, 1987.

58. Bundle, D.R., Cherwonogrodzky, J.W., Caroff, M. and Perry, M.B. The lipopolysaccharides of

Brucella abortus and B. melitensis. Ann. Inst. Pasteur/Microbiol., 138, 92-98, 1987.

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59. Sugden, E.A., Samagh, B.S., Bundle, D.R. and Duncan, J.R. Lipoarabinomannan and lipid-free

arabinomannan antigens of Mycobacterium paratuberculosis. Infect. Immun.. 55, 762-770,

1987.

60. Bundle, D.R., Cherwonogrodzky, J.W. and Perry, M.B. The structure of the lipopolysaccharide

O-chain (M antigen) and polysaccharide B produced by Brucella melitensis 16M. FEBS Letters,

216, 261-264, 1987.

61. Carlin, N.I.A., Bundle, D.R. and Lindberg, A.A. Characterization of five Shigella flexneri

variant Y - specific monoclonal antibodies using defined saccharides and glycoconjugate

antigens. J. Immunol., 138, 4419-4427, 1987.

62. Cherwonogrodzky, J.W., Perry, M.B. and Bundle, D.R. Identification of the A and M antigens

of Brucella as the O-polysaccharides of smooth lipopolysaccharides. Can. J. Microbiol., 33, 979-

981, 1987.

63. Altman, E., Brisson, J.-R., Bundle, D.R. and Perry, M.B. Structural studies of the O-chain of

the phenol-phase soluble lipopolysaccharide from Haemophilus pleuropneumoniae serotype 2.

Biochem. Cell Biol., 65, 876-889, 1987.

64. Di Fabio, J.L., Perry, M.B. and Bundle, D.R. Analysis of the lipopolysaccharide of

Pseudomonas maltophilia 555. Biochem. Cell. Biol., 65, 968-977, 1987.

65. Bundle, D.R., Cherwonogrodzky, J.W. and Perry, M.B. Structural elucidation of the Brucella

melitensis M antigen by high resolution NMR at 500 MHz. Biochemistry, 26, 8717-8726, 1987.

66. Gerken, M. and Bundle, D.R. Synthesis of immunologically active oligosaccharide determinants

of the Brucella A antigen: utilization of intermediates derived from methyl 4-azido-4,6-dideoxy-

-D-mannopyranoside. Tet. Lett., 28, 5067-5070, 1987.

67. Peters, T. and Bundle, D.R. Synthesis of 4,6-dideoxy-4-formamido--D- mannose containing

tri- tetra- and pentasaccharides, antigenic determinants of the Brucella A and M antigens. J.

Chem. Soc. Chem. Comm., 1648-1650, 1987.

68. Bundle, D.R., Gerken, M. and Peters, T. Synthesis of antigenic determinants of the Brucella A

antigen utilizing methyl 4-azido-4,6-dideoxy--D-mannopyranoside efficiently derived from D-

mannose. Carbohydr. Res., 174, 239-251, 1988.

69. Bundle, D.R., Cherwonogrodzky, J.W. and Perry, M.B. Characterization of Brucella

polysaccharide B. Infect. Immun., 56, 1101-1106, 1988.

70. Kramer, J.K.G., Sauer, F.D. and Bundle, D.R. The presence of tightly bound Na+ or K+ in

glycolipids in Methanobacterium thermoautotrophicum. Biochim. Biophys. Acta., 961, 285-

292, 1988.

71. Todd, E.C.D., Szabo, R.A., Peterkin, P., Sharpe, A.N, Parrington, L., Bundle, D.R., Gidney,

M.A.J. and Perry, M.B. Rapid hydrophobic grid membrane filter -enzyme labeled antibody

procedure for identification and enumeration of Escherichia coli 0157 in foods. Applied and

Environmental Microbiology, 54, 2536-2540, 1988.

72. Perry, M.B., Bundle, D.R., Gidney, M. A. J. and Lior, H. Identification of Escherichia coli

serotype 0157 strains by using monoconal antibody. J. Clin. Microbiol., 26, 2391-2394, 1988.

73. Kulakowska, M., Lugowski, C., Romanowska, E. and Bundle, D.R. The comparison of

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monoclonal-antibodies specific for 2 general epitopes located on citrobacter-036

lipopolysaccharide. Carbohydr. Res., 178, 233-241, 1988.

74. Zygmunt, M.S., Dubray, G., Bundle, D.R. and Perry, M.B. Purified native haptens of Brucella

abortus B19 and B. melitensis 16 M reveal the lipopolysaccharide origin of the antigens. Ann.

Inst. Pasteur/Microbiol., 139, 421-433, 1988.

75. Bundle, D.R. Antibody combining sites and oligosaccharide determinants studied by

competitive binding, sequencing and X-ray crystallography. Pure and Applied Chem., 61, 1171-

1180, 1989.

76. Peters, T. and Bundle. D.R. Synthetic antigenic determinants of the Brucella A polysaccharide;

a disaccharide thioglycoside for block synthesis of pentasaccharide and lower homologues of

1,2-linked 4,6-dideoxy-4-formamido--D-mannose. Can. J. Chem., 67, 491-496, 1989.

77. Peters, T. and Bundle, D.R. Block synthesis of two pentasaccharide determinants of the Brucella

M antigen using thioglycoside methodologies. Can. J. Chem., 67, 497-502, 1989.

78. Pinto, B.M., Reimer, K.B., Morissette, D.G. and Bundle, D.R. Oligosaccharides corresponding

to biological repeating units of Shigella flexneri variant Y polysaccharide. Synthesis and two-

dimensional NMR analysis of a hexasaccharide hapten. J. Org. Chem., 54, 2650-2656, 1989.

79. Nielsen, K., Cherwonogrodzky, J.W., Duncan, J.R. and Bundle, D.R. Enzyme-linked

immunosorbent assay for differentiation of the antibody response of cattle naturally infected with

Brucella abortus or vaccinated with strain 19. Am. J. Vet. Res., 50, 5-9, 1989.

80. Bundle, D.R., Cherwonogrodzky, J.W., Gidney, M.A.J., Meikle, P.J., Perry, M.B. and Peters, T.

Definition of Brucella A and M epitopes by monoclonal typing reagents and synthetic

oligosaccharides. Infect. Immun., 57, 2829-2836, 1989.

81. Meikle, P.J., Perry, M.B., Cherwonogrodzky, J.W. and Bundle, D.R. Fine structure of A and M

antigens from Brucella biovars. Infect. Immun., 57, 2820-2828, 1989.

82. Pinto, B.M., Reimer, K.B., Morissette, D.G. and Bundle, D.R. Oligosaccharides corresponding

to biological repeating units of Shigella flexneri variant Y polysaccharide: Part III. Synthesis

and 2D NMR analysis of a heptasaccharide hapten. J. Chem. Soc. Perkin I, 293-299, 1990.

83. Pinto, B.M., Reimer, K.B., Morissette, D.G. and Bundle, D.R. Synthesis and 2D-n.m.r. analysis

of a pentasaccharide glycoside of the biological repeating units of Shigella flexneri variant Y

polysaccharide and the preparation of a synthetic antigen. Carbohydr. Res., 196, 156-166, 1990.

84. Perry, M.B. and Bundle, D.R. Antigenic relationships in the lipopolysaccharides of strains of

Escherichia hermannii with Escherichia coli 0157:H7, Brucella melitensis and Brucella abortus.

Infect. Immun. 58, 1391-1395, 1990.

85. Peters, T., Brisson, J.-R. and Bundle, D.R. Conformational analysis of key disaccharide

components of Brucella A and M antigens. Can. J. Chem., 68, 979-988, 1990.

86. Kihlberg, J.O., Leigh, D.A. and Bundle, D.R. The in situ activation of thioglycosides with

bromine: An improved glycosylation method. J. Org. Chem., 55, 2860-2863, 1990.

87. Anand, N.N., Dubuc, G., Mandal, S., Phipps, J., Gidney, M.A.J., Sinnott, B., Young, N.M.,

MacKenzie, C.R., Bundle, D.R. and Narang, S.A. Synthesis and expression in Escherichia coli

of DNA encoding the murine 1 chain of a monoclonal antibody specific for Salmonella

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serotype B O-antigen. Protein Engineering, 3, 541-546, 1990.

88. Beynon, L.M., Bundle, D.R. and Perry, M.B. The structure of the antigenic lipopolysaccharide

O-chain produced by Escherichia hermanii ATCC 33650 and 33652. Can. J. Chem., 68, 1456-

1466, 1990.

89. Vorberg, E. and Bundle, D.R. Carbohydrate-enzyme conjugates for competitive EIA. J.

Immunol. Meth., 132, 81-89, 1990.

90. Meikle, P.J. and Bundle, D.R. Preparation of polysaccharide enzyme conjugates for competitive

binding assays. Glycoconjugate J., 7, 207-218, 1990.

91. Meikle, P.J., Young, N.M. and Bundle, D.R. O-antigen biotin conjugates: Preparation and use

in direct competitive enzyme immunoassays. J. Immunol. Meth., 132, 255-261, 1990.

92. Rose, D.R., Cygler, M., To, R.J., Przybylska, M., Sinnott, B. and Bundle, D.R. Preliminary

crystal structure determination of an Fab specific for a Salmonella O-polysaccharide antigen. J.

Mol. Biol., 215, 489-492, 1990.

93. Kihlberg, J., Eichler, E. and Bundle, D.R. The design and synthesis of antibody binding site

probes: three pentasaccharide analogues of the Brucella A antigen prepared by in situ activation

of thioglycosides with bromine. Carbohydr. Res., 211, 59-75, 1991.

94. Sigurskjold, B.W., Altman, E. and Bundle, D.R. Sensitive titration microcalorimetric study of

the binding of Salmonella O-antigenic oligosaccharide by a monoclonal antibody. Eur. J.

Biochem., 197, 239-246, 1991.

95. Oomen, R., Young, N.M. and Bundle, D.R. Molecular modeling of antibody-antigen complexes

between the Brucella abortus O-chain polysaccharide and a specific monoclonal antibody.

Protein Engineering, 4, 427-433, 1991.

96. Auzanneau, F.-I. and Bundle, D.R. Incidence and avoidance of stereospecific 1,2-thioethyl

migration during the synthesis of ethyl 1-thio--L-rhamnopyranoside 2,3-orthoester. Carbohydr.

Res., 212, 13-24, 1991.

97. Eichler, E., Kihlberg, J. and Bundle, D.R. Access to fluorescent probes via allyl glycosides; the

synthesis of a Brucella trisaccharide epitope linked to a coumarin. Glycoconjugate J., 8, 69-74,

1991.

98. Kihlberg, J. and Bundle, D.R. The synthesis of antibody binding site probes: A hexasaccharide

and two pentasaccharides related to the Brucella A antigen prepared by in situ activation of

thioglycosides with bromine. Carbohydr. Res., 216, 67-78, 1991.

99. Anand, N.N., Dubuc, G., Phipps, J., MacKenzie, C.R., Sadowska, J., Young, N.M., Bundle, D.R.

and Narang, S.A. Synthesis and expression in Escherichia coli of cistronic DNA encoding an

antibody fragment specific for a Salmonella serotype B O-antigen. Gene, 100, 39-44, 1991.

100. Cygler, M., Rose, D.R. and Bundle, D.R. Recognition of a cell surface oligosaccharide epitope

of pathogenic Salmonella by an antibody Fab fragment. Science, 253, 442-446, 1991.

101. Anand, N.N., Mandal, S., MacKenzie, C.R., Sadowska, J., Sigurskjold, B., Young, N.M.,

Bundle, D.R. and Narang, S.A. Bacterial Expression and Secretion of Various Single-Chain Fv

Genes Encoding Proteins Specific for a Salmonella Serotype B O-Antigen. J. Biol. Chem., 266,

21874-21879, 1991.

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102. Narang, S.A., Brummell, D.A., Sharma, V., Bilous, D., Dubuc, G., MacKenzie, C.R.,

Michniewicz, J., Sadowska, J., Anand, N.N., Young, N.M. and Bundle, D.R. Scanning of key

residues in antibody binding sites by two saturation-mutagenesis approaches. Nucleic Acid Res.,

24, 173-179, 1991.

103. Sigurskjold, B. and Bundle, D.R. Thermodynamics of oligosaccharide binding to a monoclonal

antibody specific for a Salmonella O-antigen point to hydrophobic interactions in the binding

site. J. Biol. Chem., 267, 8371-8376, 1992.

104. Reimer, K.B., Gidney, M.A.J., Bundle, D.R. and Pinto, B.M. Immunochemical characterization

of polyclonal and monoclonal streptococcus group A antibodies by chemically defined

glycoconjugates and synthetic oligosaccharides. Carbohydr. Res., 232, 131-142, 1992.

105. Hanna, H.R. and Bundle, D.R. Antibody-oligosaccharide interactions: The synthesis of 2-deoxy-

-L-rhamnose containing oligosaccharide haptens related to Shigella flexneri variant Y antigen.

Can. J. Chem., 71, 125-134, 1993.

106. Auzanneau, F.-I., Hanna, H.R. and Bundle, D.R. The synthesis of chemically modified

disaccharide derivatives of the Shigella flexneri Y polysaccharide antigen. Carbohydr. Res.,

240, 161-181, 1993.

107. Brummell, D.A., Sharma, V.P., Anand, N.N., Bilous, D., Dubuc, G., Michniewicz, J.,

MacKenzie, C.R., Sadowska, J., Sigurskjold, B.W., Sinnott, B., Young, N.M., Bundle, D.R.,

Narang, S.A. Probing the combining site of an anti-carbohydrate antibody by saturation-

mutagenesis: role of the heavy chain CDR3 residues. Biochemistry, 32, 1180-1187, 1993.

108. Vyas, M.N., Vyas, N.K. Meikle, P.J., Sinnott, B., Pinto, B.M., Bundle, D.R. and Quiocho, F.A.

Preliminary crystallographic analysis of a Fab specific for the O-antigen of Shigella flexneri cell

surface lipopolysaccharide with and without bound saccharides. J. Mol. Biol., 231, 133-136,

1993.

109. Auzanneau, F.-I. and Bundle, D. R. Application of thioglycoside chemistry to the synthesis of

trisaccharides and deoxy-trisaccharides related to the Shigella flexneri Y polysaccharide. Can. J.

Chem., 71, 534-548, 1993.

110. Baumann, H., Altman, E. and Bundle, D. R. Controlled acid hydrolysis of an O-antigen

fragment yields univalent heptasaccharide haptens containing one 3,6-dideoxyhexose epitope.

Carbohydr. Res., 247, 347-354, 1993.

111. Auzanneau, F.-I. and Bundle, D.R. Synthesis of chlorodeoxy trisaccharides related to the

Shigella flexneri Y polysaccharide. Carbohydr. Res., 247, 195-209, 1993.

112. Rose, D.R., Przybylska, M., To, R.J., Kayden, C.S., Oomen, R. P., Vorberg, E., Young, N.M.

and Bundle, D.R. Crystal structure to 2.45Å resolution of a monoclonal Fab specific for the

Brucella A cell wall polysaccharide antigen. Protein Science, 2, 1106-1113, 1993.

113. Uhrin, D., Brisson, J.-R. and Bundle, D.R. Pseudo-3D NMR spectroscopy: Application to oligo-

and polysaccharides. J. Biomolecular NMR, 3, 367-373, 1993.

114. Bundle, D.R., Eichler, E., Gidney, M.A.J., Meldal, M., Ragauskas, A., Sigurskjold, B.W.,

Sinnott, B., Watson, D.C., Yaguchi, M. and Young, N.M. Molecular Recognition of a

Salmonella Trisaccharide Epitope by Monoclonal Antibody SE155-4. Biochemistry, 33, 5172-

5182, 1994.

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115. Bundle, D.R., Baumann, H., Brisson, J.-R., Gagne, S.M., Zdanov, A. and Cygler, M. The

Solution Structure of a Trisaccharide-Antibody Complex: Comparison of NMR Measurements

with a Crystal Structure. Biochemistry, 33, 5183-5192, 1994.

116. Deng, S.-J., MacKenzie, C.R., Sadowska, J., Michniewicz, J., Young, N.M., Bundle, D.R. and

Narang, S.A. Selection of antibody single-chain Fvs with improved carbohydrate-binding by

phage display. J. Biol. Chem., 269, 9533-9538, 1994.

117. MacKenzie, C.R., Sharma, V., Brummell, D.A., Bilous, D., Dubuc, G., Sadowska, J., Young,

N.M., Bundle, D.R. and Narang, S.A. Effect of C-C domain switching on Fab activity and

yield in Escherichia coli: synthesis and expression of genes encoding two anti-carbohydrate

Fabs. Bio/technology, 12, 390-395, 1994.

118. Zdanov, A., Li, Y., Bundle, D.R., Deng, S.-J., MacKenzie, C.R., Narang S.A., Young, N.M. and

Cygler, M. Structure of a single-chain Fv fragment complexed with a carbohydrate antigen at

1.7Å resolution. Proc. Natl. Acad. Sci (USA), 91, 6423-6427, 1994.

119. Evans, S.V., Rose, D.R., To, R., Young, N.M. and Bundle, D.R. Exploring the mimicry of

polysaccharide antigens by anti-idiotypic antibodies: The crystallization, molecular replacement

and refinement to 2.8Å resolution of an idiotope-anti-idiotope-Fab complex and of the

unliganded-anti-idiotype Fab. J. Mol. Biol., 241, 691-705, 1994.

120. Bundle, D.R. and Eichler, E. Modulation of antibody affinity by synthetic modifications of the

most exposed pyranose residue of a trisaccharide epitope. Bioorgan. Med. Chem., 2, 1221-1229,

1994.

121. Lowary, T.L. and Bundle, D.R. Nucleophile Induced Rearrangements of Thioglycosides:

Formation of 6-Thio Glycosides and 1,6 Thioanhydrosugars Tetrahedron: Asymmetry, 5, 2397-

2404, 1994.

122. Marsden, B.J., Bundle, D.R. and Perry, M.B. Serological and structural relationships between

Escherichia coli O:98 and Yersinia enterocolitica O:11,23 and O:11,24 lipopolysaccharide O-

antigens. Biochem. Cell Biol., 72, 163-168, 1994.

123. Stangier, P., Palcic, M.M. and Bundle, D.R. 2-(Dimethyloctylsilyl)ethyl lactoside: a versatile

intermediate for chemical and enzymic ganglioside synthesis. Carbohydr. Res., 267, 153-159,

1995.

124. Evans, S.V., Sigurskjold, B.W., Jennings, H.J., Brisson, J.-R., To, R., Altman, E., Frosch, M.,

Weisgerber, C., Kratzin, H., Klebert, S., Vaesen, M., Bitter-Suermann, D., Rose, D.R., Young,

N.M. and Bundle, D.R. The 2.8Å resolution structure, and thermodynamics of ligand binding, of

an Fab specific for (28)-polysialic acid. Biochemistry, 34, 6737-6744, 1995.

125. Deng, S.-J., MacKenzie, C.R., Hirama, T., Brousseau, R., Lowary, T., Young, N.M., Bundle,

D.R. and Narang S.A. Basis for selection of improved carbohydrate-binding single-chain

antibodies from synthetic gene libraries. Proc. Natl. Acad. Sci (USA), 92, 4992-4996, 1995.

126. Otter, A., Hindsgaul, O. and Bundle, D. R. Gradient-enhanced homonuclear 2D NMR techniques

applied to oligosaccharides containing manno-hexoses provide improved correlations for protons

coupled by small 3J. Carbohydr. Res., 275, 381-389, 1995.

127. Otter A. and Bundle, D.R., Long Range 4J and 5J Including Inter-Glycosidic Correlations in

Gradient-Enhanced Homonuclear COSY Experiments of Oligosaccharides. J. Mag. Reson. Ser.

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B, 109, 194-201, 1995.

128. Lowary, T., Eichler, E. and Bundle, D.R. Synthesis of a pentasaccharide epitope for the

investigation of carbohydrate-protein interactions. J. Org. Chem., 60, 7316-7327, 1995.

129. MacKenzie, C.R., Clark, I.D., Evans, S.V., Hill, I.E., MacManus, J.P., Dubuc, G., Bundle, D.R.,

Narang S.A., Young, N.M. and Szabo, A.G. Bifunctional fusion proteins consisting of a single-

chain antibody and an engineered lanthanide-binding protein. Immunotechnology, 1, 139-150,

1995.

130. Seto, N.O.L., Palcic, M.M., Hindsgaul, O., Bundle, D.R. and Narang, S.A. Expression of a

recombinant human glycosyltransferase from a synthetic gene and its utilization for synthesis of

the human blood group B trisaccharide. Eur. J. Biochem., 234, 323-328, 1995.

131. MacKenzie, C.R., Hirama, T., Deng, S.-J., Bundle, D.R., Narang S.A. and Young, N.M.

Analysis by surface plasmon resonance of the influence of valence on the ligand binding affinity

and kinetics of an anti-carbohydrate antibody. J. Biol. Chem., 271, 1527-1533, 1996.

132. Zhang, J., Otter A. and Bundle D.R. Synthesis and Conformational Studies of the Tyvelose

Capped, Lewis-x Like Tetrasaccharide Epitope of Trichinella spiralis. Bioorgan. Med. Chem., 4,

1989-2001, 1996.

133. Probert, M.A., Zhang, J. and Bundle D.R. Synthesis of and linked Tyvelose Epitopes of the

Trichinella spiralis glycan; 2-Acetamido-2-deoxy-3-O-(3,6-dideoxy-D-arabino-hexopyranosyl)-

-D-galactopyranosides. Carbohydr. Res., 296, 149-170, 1996.

134. Ellis, L.A., McVay, C.S., Probert, M.A., Zhang, J., Bundle, D.R. and Appleton J.A. Terminal -

linked tyvelose creates unique epitopes in Trichinella spiralis glycan antigens. Glycobiology, 7,

383-390, 1997

135. Seto, N.O.L., Palcic, M.M., Compston, C.A., Li, H., Bundle, D.R. and Narang, S.A. Sequential

interchange of four amino acids from blood group B to blood group A glycosyltransferase boosts

catalytic activity and progressively modifies substrate recognition in human recombinant

enzymes. J. Biol. Chem., 272, 14133-14138, 1997.

136. Stangier, K., Palcic, M.M., Bundle, D.R., Hindsgaul, O. and Thiem, J. Fucosyltransferase-catalyzed formation of L-galactosylated Lewis structures. Carbohydr. Res., 305, 511-515, 1998.

137. Kitov, P.I., Railton, C. and Bundle, D.R. The synthesis of 16-mercaptohexadecanyl glycosides

for biosensor applications. Carbohydr. Res., 307, 361-369, 1998.

138. Bundle, D.R., Alibes, R., Nilar, S., Otter, A., Warwas, M. and Zhang, P. Thermodynamic and

conformational implications of glycosidic rotamers pre-organized for binding. J. Am. Chem.

Soc., 120, 5317-5318, 1998.

139. Alibes, R. and Bundle, D.R. Synthesis of tethered trisaccharides to probe inter-saccharide

flexibility in carbohydrate-protein interactions. J. Org. Chem., 63, 6288-6301, 1998.

140. Otter, A., Lemieux, R.U., Ball, R.G., Venot, A.P., Hindsgaul, O. and Bundle, D.R. Crystal State

and Solution Conformation of the Blood Group B Trisaccharide -L-Fucp-(12)-[ -D-Galp]-

(1 3)]--D-Galp-OCH3 Eur. J. Biochem., 259, 295-303, 1999.

141. Schriemer, D.C., Bundle, D.R., Li, L. and Hindsgaul, O. Micro-scale frontal affinity

chromatography: a new method for screening of compound libraries. Angew. Chem. Int. Ed. 37,

3383-3387, 1999.

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142. Milton, M.J. and Bundle D.R. Observation of the anti- conformation of a glycosidic linkage in

an antibody bound oligosaccharide. J. Am. Chem. Soc., 120, 10547-10548, 1998.

143. Seto, N.O.L., Compston, C.A., Evans, S. V., Bundle, D.R., Narang, S.A. and Palcic, M.M.

Donor Substrate Specificity of Recombinant Human Blood Group A, B and Hybrid A/B

Glycosyltransferases Expressed In Escherichia coli. Eur. J. Biochem. 259, 770-775, 1999.

144. Young, N.M., Gidney, M.A.J., Gudmundsson, B.M.E., MacKenzie, C.R., To, R., Watson, D.C.

and Bundle, D.R. Molecular basis for the lack of mimicry of Brucella polysaccharide antigens

by Ab2 antibodies. Mol. Immunol., 36, 339-347, 1999.

145. Wacowich-Sgarbi, S.A. and Bundle, D.R. Constrained H-Type 2 Blood Group Trisaccharide

Synthesized in a Bioactive Conformation via Intramolecular Glycosylation,

J. Org. Chem., 64, 9080-9089, 1999.

146. Yu, H.N., Zhang, P., Ling, C.-C. and Bundle, D.R. A practical route to 3,6-dideoxyhexoses.

Tetrahedron Asymmetry, 11, 465-479, 2000.

147. Kitov, P.I., Sadowska, J.M., Mulvey, G., Armstrong, G.D., Ling, H., Pannu, N.S., Read, R.J. and

Bundle, D.R. Shiga-like toxins neutralized by tailored multivalent carbohydrate ligands. Nature,

403, 669-672, 2000.

148. Alexander, J., del Guercio, M-F., Maewal, A., Qiao, L., Filkes, J. Chesnut, R.W., Paulson, J.C.,

Bundle, D,R., DeFrees, S. and Sette, A. Linear PADRE T Helper Epitope and Carbohydrate B

Cell Epitope Conjugates Induce Specific High Titer IgG Antibody Responses. J. Immunol. 164,

1625-1633, 2000.

149. Nitz, M. and Bundle, D.R. Efficient synthesis of 3,6-dideoxy--D-arabinohexopyranosyl

terminated LacdiNac glycan chains of the Trichinella spiralis parasite. J. Org. Chem., 65, 3064-

3073, 2000.

150. Nitz, M., Purse B.W. and Bundle, D.R. Synthesis of a 1,2-mannopyranosyl tetrasaccharide

found in the phosphomannan antigen of Candida albicans. Org. Let., 2, 2939-2942, 2000.

151. Zhang, P. and Bundle, D.R. Synthesis of three tethered trisaccharides to probe entropy

contributions in carbohydrate-protein interactions. Israel J. Chem., 40, 189-207, 2000.

152. Yu, H.N., Ling, C.-C. and Bundle, D.R. Efficient stereoselective synthesis of 1-thio--

mannopyranosides. JCS Perkin 1, 832-837, 2001.

153. Kitov, P.I. and Bundle, D.R. Synthesis and structure-activity relationships of di- and

trisaccharide inhibitors for Shiga-like toxin Type 1. JCS Perkin 1, 838-853, 2001.

154. Kitova, E.N., Kitov, P.I., Bundle D.R. and Klassen, J.S. The observation of multivalent

complexes of Shiga-like toxin with globotrioside and the determination of their stoichiometry by

nanoelectrospray Fourier-transform ion cyclotron resonance mass spectrometry. Glycobiology,

11, 605-611, 2001.

155. Wacowich-Sgarbi, S.A., Ling, C.C., Otter, A. and Bundle, D.R. A tethered disaccharide trapped

as its anti conformer calibrates the Karplus relationship for 3JC,H coupling constants. J. Am.

Chem. Soc., 123, 4362-4363, 2001.

156. Kitov, P.I. and Bundle, D.R. Mild oxidative one-pot allyl group cleavage. Org. Let., 3, 2835-

2838, 2001.

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157. G. Mulvey, P.I. Kitov, P. Marcato, D.R. Bundle and G.D. Armstrong. Glycan mimicry as a basis

for novel anti-infective drugs. Biochimie, 83, 841-847, 2001.

158. Nitz, M. and Bundle, D.R. Synthesis of di- to hexasaccharide 1,2-linked -mannopyranan

oligomers, a terminal S-linked tetrasaccharide congener and the corresponding BSA

glycoconjugates. J. Org. Chem., 66, 8411- 8423, 2001.

159. Appleton, J.A., Dell, A., Nitz, M. and Bundle, D.R. Novel N-glycans of the parasitic nematode

Trichinella spiralis. Trends in Glycoscience and Glycotechnology, 13, 481-492 (2001).

160. Nitz, M., Ling, C. C., Otter, A., Cutler, J. E. and Bundle, D. R. The unique solution structure and

immunochemistry of the Candida albicans -1,2-mannopyranan cell wall antigen. J. Biol. Chem.

277, 3440-3446, 2002.

161. Soltyk, A. M., MacKenzie, C. R., Wolski, V. M., Hirama, T., Kitov, P. I., Bundle, D. R. and

Brunton, J. L. A mutational analysis of the globotriaosylceramide binding sites of verotoxin

VT1. J. Biol Chem., 277, 5351-5359, 2002.

162. Kitova, E.N., Bundle, D.R. and Klassen, J.S. Thermal Dissociation of Protein-Oligosaccharide

Complexes in the Gas Phase: Mapping the Intrinsic Intermolecular Interactions. J. Am. Chem.

Soc., 124, 5902-5913, 2002.

163. Zhang, P., Appleton, J.A., Ling, C.C. and Bundle, D.R. Synthesis of disaccharide congeners of

the Trichinella spiralis glycan and binding site mapping of two protective antibodies. Canad. J.

Chem. 80, 1141-1161, 2002.

164. Lowary, T.L., Eichler, E. and Bundle, D.R.. Oligosaccharide recognition by antibodies: synthesis

and evaluation of talose oligosaccharide analogues. Canad. J. Chem. 80, 1112-1130, 2002.

165. Yu, H.N., Ling, C.-C. and Bundle, D.R. Probing Carbohydrate-Antibody Interactions: Synthesis

of Three Salmonella Epitopes for SPR Studies. Canad. J. Chem. 80, 1131-1140 2002.

166. Uhrín, D., Prasad, A.V.K., Brisson, J.R. and Bundle, D.R. Carbohydrate-Antibody Interactions

by NMR. Antibody interactions by NMR. Canad. J. Chem. 80, 904-907, 2002.

167. Vyas, N.K., Vyas, M.N., Chervenak, M.C., Johnson,

M.A., Pinto, B.M., Bundle, D.R. and

Quiocho, F.A. Molecular Recognition of Oligosaccharide Epitopes by a Monoclonal Fab

Specific for Shigella flexneri Y Lipopolysaccharide: X-ray Structures and Thermodynamics.

Biochemistry 41, 13575-13586, 2002.

168. Kitova, E.N., Bundle, D.R. and Klassen, J.S. Evidence for the Preservation of Specific

Intermolecular Interactions in Gaseous Protein-Oligosaccharide Complexes. J. Am. Chem. Soc.,

124, 9340-9341, 2002.

169. Kitova, E.N., Wang, W., Bundle, D.R. and Klassen, J.S. Retention of Bioactive Ligand

Conformation in a Gaseous Protein-Trisaccharide Complex. J. Am. Chem. Soc., 124, 13980-

13981, 2002.

170. Mulvey, G.L., Marcato, P., Kitov, P.I., Sadowska, J., Bundle, D.R. and Armstrong, G.D.

Assessment in Mice of the Therapeutic Potential of tailored, Multivalent Shiga Toxin

Carbohydrate Ligands. J. Infect. Dis., 187, 640-649, 2003.

171. Kitov, P.I., Shimizu, H., Homans, S.W. and Bundle, D.R. Optimization of Tether Length in non-

Glycosidically Linked Bivalent Ligands that Target Sites 2 and 1 of Shiga-like Toxin. J. Am.

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Chem. Soc., 125, 3284-3294, 2003.

172. Kamath, V., Sadowska, J., Nilar, S., Bundle, D.R., Hindsgaul, O. Synthetic analogs of the

Lewisb-tetrasaccharide and their binding to the lectin GS-IV – Part 1. Synlett, 1327-1330, 2003.

173. Yung, A.,Turnbull, B., Kalverda, A., Thompson, G., Homans, S., Kitov, P.I. and Bundle, D.R.

Large scale millisecond inter-subunit dynamics in the B subunit homopentamer of the toxin

derived from E. coli O157. J. Am. Chem. Soc., 125, 13058-13062, 2003.

174. Kitov, P.I. and Bundle, D.R. On the Nature of the Multivalency Effect: A Statistical

Thermodynamic Model J. Am. Chem. Soc., 125, 16271-16284, 2003.

175. Vyas, N.K., Vyas, M.N., Chervenak, M.C., Bundle, D.R., Pinto, B.M. and Quiocho, F.A.

Structural basis of peptide-carbohydrate mimicry in an antibody-combining site. Proc. Natl.

Acad. Sci (USA), 100, 15023-15028, 2003.

176. Rich, J.R., Szpacenko, A., Palcic, M.M. and Bundle, D.R. Glycosyltransferase catalyzed

synthesis of thiooligosaccharides. Angew. Chem. Int. Ed., 43, 613-615, 2004.

177. Willison, H.J., Townson, K., Veitch, J., Boffey, J., Isaacs, N. andersen, S., Zhang, P., Ling, C.-C.

and Bundle, D.R. Synthetic disialylgalactose immunoadsorbents deplete anti-GQ1b antibodies

from neuropathy sera. Brain, 127, 680-691, 2004.

178. Andersen, S., Ling, C.-C., Zhang, P., Townson, K., Willison, H.J. and Bundle, D.R. Synthesis of

ganglioside epitopes for oligosaccharide specific immunoadsorption therapy of Guillian Barré

syndrome. Org. Biomol. Chem., 2, 1199 – 1212, 2004.

179. Kitova, E., Bundle, D.R. and Klassen, J.S. Partitioning of solvent effects and intrinsic

interactions in biological recognition. Angew. Chem. Int. Ed., 43, 4183-4186, 2004.

180. Rich, J. and Bundle, D.R. S-Linked ganglioside analogues for use in conjugate vaccines. Org.

Lett., 6(6), 897-900, 2004.

181. Wu, X., Ling, C.-C. and Bundle, D.R. A New Homobifunctional p-Nitro Phenyl Ester Coupling

Reagent for the Preparation of Neoglycoproteins. Org. Lett., 6(24), 4407-4410, 2004.

182. Gagne, R.A., McGavin, R.S., Chervenak, M.C. and Bundle, D.R. The design, synthesis and

evaluation of high affinity macrocyclic carbohydrate inhibitors. Org. Biomol. Chem., 3, 2723-

2732, 2005.

183. McGavin, R.S. and Bundle, D.R. Developing high affinity oligosaccharide inhibitors:

conformational pre-organization paired with functional group modification. Org. Biomol. Chem.,

3, 2733-2740, 2005.

184. Ho, J.G.S., Kitov, P.I., Paszkiewicz, E., Sadowska, J., Bundle, D.R. and. Ng, K.K.-S. Ligand-

assisted aggregation of proteins: dimerization of serum amyloid P component by bivalent

ligands. J. Biol. Chem., 280, 31999-32008, 2005.

185. Wu, X. and Bundle, D.R. Synthesis of glycoconjugate vaccines for Candida albicans using novel

linker methodology. J. Org. Chem., 70, 7381-7388, 2005.

186. Cai, Y., Ling, C.-C. and Bundle, D. R. A facile approach to 2-acetamido-deoxy--D-

glucopyranosides via the furanosyl oxazoline. Org. Lett., 7, 4021-4024, 2005.

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187. Solomon, D., Kitov, P. I., Paszkiewicz, E., Grant, G. A., Sadowska, J. M.. and Bundle, D. R.

Hetero-bifunctional multivalent inhibitor-adaptors mediate specific aggregation between shiga

toxin and a pentraxin. Org. Lett., 7, 4369-4372, 2005.

188. Kanda, V. Kitov, P.I., Bundle, D.R. and McDermott, M.T. Surface plasmon resonance imaging

measurements of the inhibition of Shiga-like toxin by synthetic multivalent inhibitors. Anal.

Chem. 77, 7497-7504, 2005.

189. Bundle, D.R. Rich, J.R., Jacques, S., Yu, H.N., Nitz, M. and Ling, C.-C. Thio-oligosaccharide

conjugate vaccines evoke antibodies specific for native antigens. Angew. Chem. Int. Ed., 44,

7725-7729, 2005.

190. Rich, J.R., Wakarchuk, W.W. and Bundle, D.R. Chemical and chemoenzymatic synthesis of S-

linked ganglioside analogues and their protein conjugates. Immunogens with improved in vivo

availability? Chem. Eur. J., 12, 845-858, 2006.

191. Jacques, S., Rich, J.R., Ling, C.-C. and Bundle, D.R. Chemoenzymatic synthesis of GM3 and

GM2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis

and solid phase applications. Org. Biomol. Chem., 4, 142-154, 2006.

192. Cai, Y., Ling, C.-C. and Bundle, D.R. A general, efficient and stereospecific route to

sphingosine, sphinganines, phytosphingosines and their analogs. Org. Biomol. Chem., 4, 1140-

1146, 2006.

193. Bundle, D.R. Nitz, M., Wu, X. and Sadowska, J.M. A uniquely small, protective carbohydrate

epitope may yield a conjugate vaccine for Candida albicans. Amer. Chem. Soc., Symp. Ser., 989,

163-183, 2007.

194. Townson, K., Boffey, J., Nicholl, D., Veitch, J., Bundle, D.R., Zhang, P., Samain, E., Antoine,

T., Bernardi, A., Arosio, D., Sonnino, S., Isaacs, N. and Willison, H.J. Solid phase

immunoadsorption for therapeutic and analytical studies on neuropathy-associated anti-GM1

antibodies. Glycobiology, 17, 294–303, 2007.

195. Kitova, E.N., Kitov, P.I., Paszkiewicz, E., Kim, J., Mulvey, G.L., Armstrong, G.D., Bundle, D.R.

and Klassen, J.S. Affinities of Shiga Toxins 1 and 2 for Univalent and Oligovalent Pk

Trisaccharide Analogs Measured by Electrospray Ionization Mass Spectrometry. Glycobiology,

17, 1156-1166, 2007.

196. Wu, X., Lipinski, T., Carrell, F., Bailey, J. J., and Bundle, D. R. Synthesis and Immunochemical

Studies on a Candida albicans Clustered Glycoconjugate Vaccine. Org. Biomol. Chem., 5, 3477

– 3485, 2007.

197. Moore, S. L., Uitz, C., Ling, C.-C., Bundle, D. R., Fusco P. C. and Michon, F. Epitope

Specificities of the Groups Y and W-135 Polysaccharides of Neisseria meningitides. Clinical

and Vaccine Immunology, 14, 1311-1317, 2007.

198. Kitov, P. I., Lipinski, T., Paszkiewicz, E., Solomon, D., Sadowska, J. M., Grant, G. G. A.,

Mulvey, G. L., Kitova, E. N., Klassen, J. S., Armstrong, G. D. and Bundle, D. R. An

Entropically Efficient Supramolecular Inhibition Strategy for Shiga Toxins. Angew. Chemie Intl.

Ed., 47, 672-676, 2008.

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199. O’Reilly, M. K., Collins, B. E., Han, S., Liao, L., Rillahan, C. Kitov, P. I., Bundle, D. R. and

Paulson, J. C. Bi-functional CD22 ligands use multimeric immunoglobulins as protein scaffolds

in assembly of immune complexes on B cells. J. Am. Chem. Soc., 130, 7736-7745, 2008.

200. Dziadek, S., Jacques, S. and Bundle, D. R. A novel linker methodology for the synthesis of

tailored conjugate vaccines composed of complex carbohydrate antigens and specific TH-cell

peptide epitopes. Chem. Eur. J., 14, 5908-5917, 2008.

201. Wu, X., Lipinski, T., Paszkiewicz, E. and Bundle, D. R. Synthesis and immunochemical

characterization of S-linked glycoconjugate vaccines against Candida albicans

Chem. Eur. J., 14, 6474-6482, 2008.

202. Xin , H., Dziadek, S., Bundle, D. R. and Cutler, J. Synthetic glycopeptide vaccines combining β-

mannan and peptide epitopes induce protection against candidiasis. Proc. Natl. Acad. Sci (USA),

105, 13526-13531, 2008.

203. Kitov, P. I., Mulvey, G. L., Griener, T., Lipinski, T., Solomon, D., Paszkiewicz, E., Jacobson, J.

, Sadowska, J. M., Suzuki, M., Yamamura, K., Armstrong, G. D. and Bundle, D. R. In vivo

supramolecular templating enhances the activity of multivalent ligands: A potential therapeutic

against the E. coli O157 AB5 toxins. Proc. Natl. Acad. Sci (USA), 105, 16837-16842, 2008.

204. Grant, C.F., Kanda, V., Yu, H., Bundle, D.R. and McDermott, M.T. Optimization of

Immobilized Bacterial Disaccharides for Surface Plasmon Resonance Imaging Measurements of

Antibody Binding. Langmuir, 24, 14125–14132, 2008.

205. Cai, Y., Ling, C.-C. and Bundle, D.R. Concise and efficient synthesis of 2-acetamido-2-deoxy-β-

D-hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-β-D-glucose. J. Org.

Chem., 74, 580–589, 2009.

206. Nycholat, C.M., and Bundle, D.R. Synthesis of mono-deoxy and mono-O-methyl congeners of

methyl β-D-mannopyranosyl-(12)-β-D-mannopyranoside for epitope mapping of anti-Candida

albicans antibodies. Carbohydr. Res., 344, 555-569, 2009.

207. Cai, Y., Ling, C.-C. and Bundle, D.R. Efficient Synthesis of D-xylo and D-ribo-

Phytosphingosines from methyl 2-amino-2-deoxy-β-D-hexopyranosides. Carbohydr. Res., 344,

2120-2126, 2009.

208. Hu, J., Huang, X., Ling, C.-C., Bundle, D.R. and Cheung, N.K. Reducing Epitope Spread during

Affinity Maturation of an Anti-Ganglioside GD2 Antibody. J. Immunol., 183, 5748 – 5755,

2009.

209. Wu, X., Cui, L., Lipinski, T. and Bundle, D.R. Synthesis of monomeric and

dimeric repeating units of the zwitterionic type 1 capsular polysaccharide

from Streptococcus pneumoniae. Chem. Eur. J., 16, 3476-3488, 2010.

210. Iynkkaran, I. and Bundle, D. R., A novel glycosyl donor for synthesis of 2-acetamido-4-amino-

2,4,6-trideoxy-α-D-galactopranosides. Carbohydr. Res., 345, 2323-2327, 2010.

211. Huang, J., Motto D. G., Bundle, D. R. and Sadler, J. E. Shiga toxin B subunits induce VWF

secretion by human endothelial cells and thrombotic microangiopathy in ADAMTS13-deficient

mice. Blood, 116, 3653-3659, 2010.

212. Lipinski, T., Kitov, P., Szpacenko, A., Paszkiewicz, E. and Bundle, D. R. Synthesis and

Immunogenicity of a Glycopolymer Conjugate. Bioconjug. Chem., 22, 274-281, 2011.

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213. Tran, H.-A., Kitov, P. I., Paszkiewicz, E., Sadowska, J. M. and Bundle, D. R. Multifunctional

multivalency: a focused library of polymeric cholera toxin antagonists. Org. Biomol. Chem., 9,

3658-3671, 2011.

214. Guiard, J., Langpap, B., Kitov, P., Peters, P. and Bundle, D. R. “Double-Click” Protocol for

Synthesis of Heterobifunctional Multivalent Ligands: Toward a Focused Library of Specific

Norovirus Inhibitors. Chem. Eur. J., 17, 7438-7441, 2011.

215. Rademacher, C., Guiard, J., Kitov, P., Langpap, B., Dalton, K. P., Parra, F., Bundle, D. R. and

Peters, P. Targeting Norovirus Infection – Multivalent Entry Inhibitor based on NMR Data.

Chem. Eur. J., 17, 7442-7453, 2011.

216. Cui, L., Kitov, P. I., Completo, G. C., Paulson, J. C. and Bundle. D. R. Supramolecular

Complexing of Membane Siglec CD22 Mediated by a Polyvalent Heterobifunctional Ligand that

Templates on IgM. Bioconjug. Chem., 22, 546-550, 2011.

217. Lipinski, T., Luu, T., Kitov, P. I., Szpacenko, A. and Bundle, D. R. A structurally diversified

linker enhances the immune response to a small carbohydrate hapten. Glycoconj. J., 28, 149-164,

2011.

218. Sandbhor, M. S., Soya, N, Albohy, A., Zheng, R. B., Cartmell, J., Bundle, D. R., Klassen, J. S.

and Cairo, C. W. Substrate recognition of the membrane-associated sialidase NEU3 requires a

hydrophobic aglycone. Biochemistry, 50, 6753-5762, 2011.

219. Kitov, P. I., Paszkiewicz, E., Sadowska, J.M., Deng, Z., Ahmed, M., Narain, R., Griener, T.,

Mulvey, G. L., Armstrong, G. D., Bundle, D. R. Impact of the nature and size of the polymeric

backbone on the ability of heterobifunctional ligands to mediate Shiga toxin and serum amyloid

P component ternary complex formation. Toxins, 3, 1065-1088, 2011.

220. Zhang, P., Razi, N., Eugenio, L., Fentabil, M., Kitova, E.N., Klassen, J.S., Bundle, D.R., Ng,

K.K.-S. and Ling, C.-C. Unexpected structure of a Clostridium difficile toxin A ligand

necessitates an annotation correction in a popular screening library. Chem. Comm. 47, 12397-

12399, 2011.

221. Costello, C. and Bundle, D. R. Synthesis of three trisaccharide congeners to investigate frame

shifting of β1,2-mannan homo-oligomers in an antibody binding site. Carbohydr. Res., March

2012 in press. http://dx.doi.org/10.1016/j.carres.2012.03.019,

222. Xin, H., Cartmell, J., Bailey, J. J., Dziadek, S., Bundle, D. R. and Cutler, J. E. Self -adjuvanting

Glycopeptide Conjugate Vaccine against Disseminated Candidiasis. PLoS One 7, e35106, 2012.

223. Johnson, M. A., Cartmell, J., Weisser, N. E., Woods, R. J., Bundle, D. R. Molecular recognition

of Candida albicans (1→2)-β-mannan oligosaccharides by a protective monoclonal antibody

reveals the immunodominance of internal saccharide residue. J. Biol. Chem.

doi:10.1074/jbc.M112.355578