Synthesis of partially O-acetylated N-acetylneuraminic acid using regioselective silyl exchange technology

Org Lett. 2014 Oct 3;16(19):5044-7. doi: 10.1021/ol502389g. Epub 2014 Sep 23.

Abstract

Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C4 (2°) > C9 (1°) > C8 (2°) > C2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetylation
  • Animals
  • Molecular Structure
  • N-Acetylneuraminic Acid / chemical synthesis*
  • N-Acetylneuraminic Acid / chemistry
  • Sialic Acids / chemistry
  • Stereoisomerism

Substances

  • Sialic Acids
  • N-Acetylneuraminic Acid