The Sialic Acids Waltz: Novel Stereoselective Isomerization of the 1,7-Lactones of N-Acetylneuraminic Acids into the Corresponding γ-Lactones and Back to the Free Sialic Acids

Paola Rota, Pietro Allevi, Luigi Anastasia

Research output: Contribution to journalArticle

Abstract

An internal rearrangement of the 1,7-lactone of N-acetylneuraminic acid into its γ-lactone in high yield is reported, together with the successive conversion into the free parent sialic acid. Overall, these reactions further characterize the chemical behavior of sialic acids and their derivatives, which are increasingly considered to be key players in many biological processes, including ischemic heart disease.

Original languageEnglish
Pages (from-to)1315-1321
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume4
Issue number11
DOIs
Publication statusPublished - Nov 1 2015

Fingerprint

Sialic Acids
N-Acetylneuraminic Acid
Lactones
Isomerization
Derivatives
N-acetylneuraminic acid 1,7-lactone

Keywords

  • Carbohydrates
  • Hydrolysis
  • Lactones
  • N-acetylneuraminic acid
  • Sialic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "An internal rearrangement of the 1,7-lactone of N-acetylneuraminic acid into its γ-lactone in high yield is reported, together with the successive conversion into the free parent sialic acid. Overall, these reactions further characterize the chemical behavior of sialic acids and their derivatives, which are increasingly considered to be key players in many biological processes, including ischemic heart disease.",
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AU - Allevi, Pietro

AU - Anastasia, Luigi

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AB - An internal rearrangement of the 1,7-lactone of N-acetylneuraminic acid into its γ-lactone in high yield is reported, together with the successive conversion into the free parent sialic acid. Overall, these reactions further characterize the chemical behavior of sialic acids and their derivatives, which are increasingly considered to be key players in many biological processes, including ischemic heart disease.

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