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S1 SUPPORTING INFORMATION Enantioselective Recognition of Amino acids by Chiral Peptido-Calix[4]arenes and Thiacalix[4]arenes Joackim Bois, Isabelle Bonnamour, Christian Duchamp, Helene Parrot-Lopez, Ulrich Darbost and Caroline Felix* Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Chimie Supramoléculaire Appliquée (CSAp), CNRS, UMR 5246, 43 Boulevard du11 Novembre 1918, F-69622, Villeurbanne, France; Université de Lyon, Lyon; Université Lyon 1, Villeurbanne Contents NMR spectra (all in CDCl 3 ) Compound 4 proton (300 MHz)…………………………………………………………………………………………………………….. S3 Compound 4 carbon (75 MHz)…………………………………………………………………………...………………………………… S4 Compound 6 proton (300 MHz)…………………………………………………………………………………………………………….. S5 Compound 6 carbon (75 MHz)…………………………………………………………………………………………..…………………. S6 Compound 8a proton (300 MHz)……………………………………………………………………………………………..…………….. S7 Compound 8a carbon (75 MHz)……………………………………………………………………………………………….…………… S8 Compound 8a COSY ………..…………………………………………..…………………………………………………….…………… S9 Compound 8a NOESY………………………………………………………..……………………………………………….…………… S10 Compound 8b proton (300 MHz)…………………………………………………………………………………………….…………….. S11 Compound 8b carbon (75 MHz)……………………………………………………………………………………………….…………… S12 Compound 8b COSY……………………….………………………………………………………………………………….…………… S13 Supplementary Material (ESI) for New Journal of Chemistry This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

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Page 1: SUPPORTING INFORMATION Enantioselective Recognition of

S1

SUPPORTING INFORMATION

Enantioselective Recognition of Amino acids by Chiral Peptido-Calix[4]arenes and Thiacalix[4]arenes

Joackim Bois, Isabelle Bonnamour, Christian Duchamp, Helene Parrot-Lopez, Ulrich Darbost and Caroline Felix*

Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Chimie Supramoléculaire Appliquée (CSAp), CNRS, UMR 5246, 43 Boulevard du11 Novembre 1918, F-69622, Villeurbanne, France; Université de Lyon, Lyon; Université Lyon 1, Villeurbanne

Contents

NMR spectra (all in CDCl3)

Compound 4 proton (300 MHz)…………………………………………………………………………………………………………….. S3

Compound 4 carbon (75 MHz)…………………………………………………………………………...………………………………… S4

Compound 6 proton (300 MHz)…………………………………………………………………………………………………………….. S5

Compound 6 carbon (75 MHz)…………………………………………………………………………………………..…………………. S6

Compound 8a proton (300 MHz)……………………………………………………………………………………………..…………….. S7

Compound 8a carbon (75 MHz)……………………………………………………………………………………………….…………… S8

Compound 8a COSY ………..…………………………………………..…………………………………………………….…………… S9

Compound 8a NOESY………………………………………………………..……………………………………………….…………… S10

Compound 8b proton (300 MHz)…………………………………………………………………………………………….…………….. S11

Compound 8b carbon (75 MHz)……………………………………………………………………………………………….…………… S12

Compound 8b COSY……………………….………………………………………………………………………………….…………… S13

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 2: SUPPORTING INFORMATION Enantioselective Recognition of

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Compound 7b COSY ………..…………………………………………..…………………………………………………….…………… S14

Compound 7b NOESY………………………………………………………..……………………………………………….…………… S15

Complexe 7b- (L)-N-Ts-Val COSY………………………………….…….………………………………………………….…………… S16

Complexe 7b- (L)-N-Ts-Val NOESY……………….……………….…….………………………………………………….…………… S17

Complexe 7b- (L)-N-Ts-Val ROESY……………………….……….…….………………………………………………….…………… S18

Mass spectrometry

Complexe 7b – (L)-N-Ts Leu MS………………………………………………………………………………………………………… S19

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 3: SUPPORTING INFORMATION Enantioselective Recognition of

S3

Compound 4 proton (300 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 4: SUPPORTING INFORMATION Enantioselective Recognition of

S4

Compound 4 carbon (75 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 5: SUPPORTING INFORMATION Enantioselective Recognition of

S5

Compound 6 proton (300 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 6: SUPPORTING INFORMATION Enantioselective Recognition of

S6

Compound 6 carbon (75 MHz)

#"

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 7: SUPPORTING INFORMATION Enantioselective Recognition of

S7

Compound 8a proton (300 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 8: SUPPORTING INFORMATION Enantioselective Recognition of

S8

Compound 8a carbon (75 MHz)

$a"

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 9: SUPPORTING INFORMATION Enantioselective Recognition of

S9

Compound 8a COSY

$a"

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 10: SUPPORTING INFORMATION Enantioselective Recognition of

S10

Compound 8a NOESY

$a"

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 11: SUPPORTING INFORMATION Enantioselective Recognition of

S11

Compound 8b proton (300 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 12: SUPPORTING INFORMATION Enantioselective Recognition of

S12

Compound 8b carbon (75 MHz)

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 13: SUPPORTING INFORMATION Enantioselective Recognition of

S13

Compound 8b COSY

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Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 14: SUPPORTING INFORMATION Enantioselective Recognition of

S14

Compound 7b COSY

7b

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 15: SUPPORTING INFORMATION Enantioselective Recognition of

S15

Compound 7b NOESY

7b

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 16: SUPPORTING INFORMATION Enantioselective Recognition of

S16

Complexe 7b- (L)-N-Ts-Val COSY

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 17: SUPPORTING INFORMATION Enantioselective Recognition of

S17

Complexe 7b- (L)-N-Ts-Val NOESY

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 18: SUPPORTING INFORMATION Enantioselective Recognition of

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Complexe 7b- (L)-N-Ts-Val ROESY

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009

Page 19: SUPPORTING INFORMATION Enantioselective Recognition of

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Mass spectrometry : Complexe 7b – (L)-N-Ts Leu

Supplementary Material (ESI) for New Journal of ChemistryThis journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2009