Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers

Evan J. Horn, Jonel P. Saludes, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Sialic acid, an important carbohydrate found incorporated on the cell surface of many organisms, has been modified for use in a wide range of biological and pharmaceutical applications. We hypothesized that 4,7,8,9-tetra-O-acetyl-2-deoxy-2,3-dehydro-N-acetyl neuraminic acid methyl ester (4) could be efficiently synthesized in a one-pot reaction by heating peracetylated sialic acid (2) in pyridine and acetic anhydride to induce β-elimination. When reduced to practice, this reaction produced only modest yields of 4. Six compounds, including three new decarboxylated sialic acid dimers, were also found to have been synthesized in the reaction. In an effort to better understand the chemistry and the mechanisms of this reaction, all of the side products were isolated and fully characterized.

Original languageEnglish (US)
Pages (from-to)936-940
Number of pages5
JournalCarbohydrate Research
Volume343
Issue number5
DOIs
StatePublished - Apr 7 2008

Keywords

  • Decarboxylation
  • Neu5Ac2en
  • Sialic acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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