Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor

Simon S. Park, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

Abstract

Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

Original languageEnglish (US)
Pages (from-to)449-460
Number of pages12
JournalJournal of Antibiotics
Volume72
Issue number6
DOIs
StatePublished - Jun 1 2019

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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