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.
ASJC Scopus subject areas
- Molecular Biology