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Supporting Information
Synthesis of a truncated bi-antennary complex-type N-glycan
oxazoline; glycosylation catalysed by the endohexosaminidases
Endo A and Endo M
Thomas B. Parsons,a James W. B. Moir,b and Antony J. Fairbanksc,*
a Department of Chemistry, Chemistry Research Laboratory, University of Oxford,
Mansfield Road, Oxford, OX1 3TA, UK b Department of Biology, University of York, YO10 5YW, UK
c Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch,
New Zealand
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OO SEt
OLev
OO
Ph
1c
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
OAcO
OO
Ph
3a
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
OLevO
OO
Ph
3b
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
OHO
OO
Ph
3c
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
O
OAcOO
Ph
4a
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
HO
OAcOO
Ph
4b
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OAcOAcO
PhthN
OAc
OAcO
O
AcOAcO
SEt6b
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
O
OAcOO
Ph
O
O OAcOAcOAc
OAcO
AcOAcO
PhthN7
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
O
OAcHOBnO
O
OOAc
OAcOAc
OAcO
AcOAcO
PhthN 8
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOBnO OPMP
PhthN
OBnO
O
OAcOBnO
O
OOAc
OAcOAc
OAcO
AcOAcO
PhthN
OAcOAcO
PhthN
OAc
OAcO
O
AcOAcO
9a
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOAcO OPMP
PhthN
OAcO
O
OAcOAcO
O
OOAc
OAcOAc
OAcO
AcOAcO
PhthN
OAcOAcO
PhthN
OAc
OAcO
O
AcOAcO
9b
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOAcO OPMP
AcHN
OAcO
O
OAcOAcO
O
OOAc
OAcOAc
OAcO
AcOAcO
AcHN
OAcOAcO
AcHN
OAc
OAcO
O
AcOAcO
9c
OOAcO
AcHN
OAcO
O
OAcOAcO
O
OOAc
OAcOAc
OAcO
AcOAcO
AcHN
OAcOAcO
AcHN
OAc
OAcO
O
AcOAcO
9d
OAc
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOAcO
OAcO
O
OAcOAcO
O
O OAcOAcOAc
OAcO
AcOAcO
AcHN
OAcOAcO
AcHN
OAc
OAcO
O
AcOAcO
N O
10
OOHO
OHO
O
OHOHO
O
O OHOHOH
OHO
HOHO
AcHN
OHOHO
AcHN
OH
OHO
O
HOHO
N O
11
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009
OOHO
OHOO
OHOHO
O
O OHOHOH
OHO
HOHO
AcHN
OHOHO
AcHN
OH
OHO
O
HOHO
13
OO HN
OHO
CbzNH
CO2MeNHAcHONHAc
Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2009