Synthesis of 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-D-galacto se by the sequential use of beta-D-galactosidases from bovine testes and Escherichia coli

L Hedbys; E Johansson; K Mosbach; P O Larsson

doi:10.1016/0008-6215(89)84036-4

Synthesis of 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-D-galacto se by the sequential use of beta-D-galactosidases from bovine testes and Escherichia coli

Carbohydr Res. 1989 Mar 15;186(2):217-23. doi: 10.1016/0008-6215(89)84036-4.

Authors

L Hedbys¹, E Johansson, K Mosbach, P O Larsson

Affiliation

¹ Department of Pure and Applied Biochemistry, University of Lund, Sweden.

PMID: 2500235
DOI: 10.1016/0008-6215(89)84036-4

Abstract

beta-D-Galp-(1----3)-D-GalNAc (1) was synthesised from lactose and GalNAc on a mmolar scale by transgalactosylation using beta-D-galactosidase from bovine testes. The large proportions of unwanted oligosaccharides in the product mixture were removed by treatment with beta-D-galactosidase from E. coli, which left 1, monosaccharides, and a small proportion of trisaccharides. Carbon-Celite chromatography then gave 1 in a yield of 21% based on the GalNAc added.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylgalactosamine / metabolism
Animals
Antigens, Tumor-Associated, Carbohydrate*
Carbohydrate Conformation
Cattle
Chromatography, Gas
Disaccharides / biosynthesis*
Drug Stability
Escherichia coli / enzymology*
Galactosidases / metabolism*
Gas Chromatography-Mass Spectrometry
Hydrolysis
Lactose / metabolism
Male
Substrate Specificity
Testis / enzymology*
beta-Galactosidase / metabolism*

Substances

Antigens, Tumor-Associated, Carbohydrate
Disaccharides
Thomsen-Friedenreich antigen
Galactosidases
beta-Galactosidase
Lactose
Acetylgalactosamine