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

Simon S. Park, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)5044-5047
Number of pages4
JournalOrganic Letters
Volume16
Issue number19
DOIs
StatePublished - Oct 3 2014

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N-Acetylneuraminic Acid
Ion exchange
analogs
Technology
Acetylation
Hydrogenolysis
acids
synthesis
Ether
acetylation
hydrogenolysis
Esters
Acetates
biology
esters
acetates
ethers
pyridines
pyridine

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Synthesis of partially O-acetylated N-acetylneuraminic acid using regioselective silyl exchange technology. / Park, Simon S.; Gervay-Hague, Jacquelyn.

In: Organic Letters, Vol. 16, No. 19, 03.10.2014, p. 5044-5047.

Research output: Contribution to journalArticle

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