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

M. J. Clancy, William J. Whelan

Research output: Contribution to journalArticle

3 Citations (Scopus)

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

Fingerprint

Monosaccharides
Glucosamine
Galactose
Polymerization
Amino Sugars
Glucose
Oxidation
Saccharomyces
Disaccharides
Acetone
Yeast
Yeasts
Alcohols
metaperiodate

ASJC Scopus subject areas

  • Molecular Biology
  • Biophysics
  • Biochemistry

Cite this

@article{54041a8f64e74fba8b314c48fc35f910,
title = "Enzymic polymerization of monosaccharides. II. Synthesis of 2-acetamido-2-deoxy-6-O-(α-d-galactopyranosyl)-d-glucose (N-acetylmelibiosamine)",
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.",
author = "Clancy, {M. J.} and Whelan, {William J.}",
year = "1967",
month = "3",
day = "20",
language = "English",
volume = "118",
pages = "730--735",
journal = "Archives of Biochemistry and Biophysics",
issn = "0003-9861",
publisher = "Academic Press Inc.",
number = "3",

}

TY - JOUR

T1 - Enzymic polymerization of monosaccharides. II. Synthesis of 2-acetamido-2-deoxy-6-O-(α-d-galactopyranosyl)-d-glucose (N-acetylmelibiosamine)

AU - Clancy, M. J.

AU - Whelan, William J.

PY - 1967/3/20

Y1 - 1967/3/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0014211489&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0014211489&partnerID=8YFLogxK

M3 - Article

C2 - 4292714

AN - SCOPUS:0014211489

VL - 118

SP - 730

EP - 735

JO - Archives of Biochemistry and Biophysics

JF - Archives of Biochemistry and Biophysics

SN - 0003-9861

IS - 3

ER -