Enzymic polymerization of monosaccharides. II. Synthesis of 2-acetamido-2-deoxy-6-O-(α-d-galactopyranosyl)-d-glucose (N-acetylmelibiosamine)

M. J. Clancy, W. J. Whelan

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

2-Acetamido-2-deoxy-6-O-(α-d-galactopyranosyl)-d-glucose (N-acetylmelibiosamine) was synthesized by the catalytic action of an acetone-dried preparation of Saccharomyces carlsbergensis yeast on (a) a mixture of d-galactose and N-acetyl-d-glucosamine, and (b) a mixture of phenyl α-d-galactopyranoside and N-acetyl-d-glucosamine. A second disaccharide containing an amino sugar was isolated in reaction (a), and its structure was tentatively established as 2-acetamido-2-deoxy-3-O-(α-d-galactopyranosyl)-d-glucose. The structure of N-acetylmelibiosamine was determined by selective periodate oxidation of the derived alcohol, and the similar oxidations of related model compounds are recorded.

Original languageEnglish (US)
Pages (from-to)730-735
Number of pages6
JournalArchives of Biochemistry and Biophysics
Volume118
Issue number3
DOIs
StatePublished - Mar 20 1967
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology

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