Synthesis of α-GalNAc thioconjugates from an α-GalNAc mercaptan

Spencer Knapp, David S. Myers

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

Abstract

A variety of functionalized thioglycosides and other derivatives (10-24) of 2-acetamido-2-deoxy-1-thio-α-D-galactopyranose have been prepared in good yields and with high anomeric purities by S-substitution reactions of the sulfide anion or sulfur-centered radical from mercaptan 6. Given the importance in nature of the α-GalNAc 1-O-linkage, and the greater chemical and biological stability of the corresponding 1-S-linkage, these thioconjugates may find application in studies of synthetic vaccines, enzyme inhibitors, glycomimetic scaffolds, and other complex carbohydrate systems.

Original languageEnglish (US)
Pages (from-to)2995-2999
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number9
DOIs
StatePublished - May 3 2002

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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