mycobacterium tuberculosis arabinomannan- synthesis and ... · 11. obz br,o bno 10. 5 5 11. o ....

Synthesis and immunogenicity of Mycobacterium tuberculosis arabinomannan- CRM197 conjugate Supplementary Materials Table of Contents 1 H NMR and 13 C NMR spectra of compound 6 S1-S2 1 H NMR and 13 C NMR spectra of compound 7 S3-S4 1 H NMR and 13 C NMR spectra of compound 8 S5-S6 1 H NMR and 13 C NMR spectra of compound 9 S7-S8 1 H NMR and 13 C NMR spectra of compound 11 S9-S10 1 H NMR and 13 C NMR spectra of compound 12 S11-S12 1 H NMR and 13 C NMR spectra of compound 13 S13-S14 1 H NMR and 13 C NMR spectra of compound 14 S15-S16 1 H NMR and 13 C NMR spectra of compound 15 S17-S18 1 H NMR and 13 C NMR spectra of compound 16 S19-S20 1 H NMR and 13 C NMR spectra of compound 18 S21-S22 1 H NMR and 13 C NMR spectra of compound 19 S23-S24 1 H NMR spectra of compound 20 S25 Electronic Supplementary Material (ESI) for MedChemComm. This journal is © The Royal Society of Chemistry 2019

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Page 1: Mycobacterium tuberculosis arabinomannan- Synthesis and ... · 11. OBz Br,o Bno 10. 5 5 11. o . OTIPS OLev BnO BnO BnO BnO OBz Bno 40 CC t— t— 30 20 10 130 100 fl (ppm) 90 80

Synthesis and immunogenicity of Mycobacterium tuberculosis arabinomannan-

CRM197 conjugate

Supplementary Materials

Table of Contents

1H NMR and 13C NMR spectra of compound 6 S1-S2 1H NMR and 13C NMR spectra of compound 7 S3-S41H NMR and 13C NMR spectra of compound 8 S5-S61H NMR and 13C NMR spectra of compound 9 S7-S81H NMR and 13C NMR spectra of compound 11 S9-S101H NMR and 13C NMR spectra of compound 12 S11-S121H NMR and 13C NMR spectra of compound 13 S13-S141H NMR and 13C NMR spectra of compound 14 S15-S161H NMR and 13C NMR spectra of compound 15 S17-S181H NMR and 13C NMR spectra of compound 16 S19-S201H NMR and 13C NMR spectra of compound 18 S21-S221H NMR and 13C NMR spectra of compound 19 S23-S241H NMR spectra of compound 20 S25

Electronic Supplementary Material (ESI) for MedChemComm.This journal is © The Royal Society of Chemistry 2019