Use of human-milk fucosyltransferase in the chemoenzymic synthesis of analogues of the sialyl Lewis(a) and sialyl Lewis(x) tetrasaccharides modified at the C-2 position of the reducing unit

P V Nikrad; M A Kashem; K B Wlasichuk; G Alton; A P Venot

doi:10.1016/0008-6215(93)84162-y

Use of human-milk fucosyltransferase in the chemoenzymic synthesis of analogues of the sialyl Lewis(a) and sialyl Lewis(x) tetrasaccharides modified at the C-2 position of the reducing unit

Carbohydr Res. 1993 Dec 16;250(1):145-60. doi: 10.1016/0008-6215(93)84162-y.

Authors

P V Nikrad¹, M A Kashem, K B Wlasichuk, G Alton, A P Venot

Affiliation

¹ Alberta Research Council, Carbohydrate Research Program, Edmonton, Canada.

PMID: 8143288
DOI: 10.1016/0008-6215(93)84162-y

Abstract

Two series of trisaccharides, having the formulas alpha-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-GlcZ-OR and alpha-Neu5Ac-(2-->3)-beta-D-Gal-(1-->3)-beta-D-GlcZ-OR [R = (CH2)8CO2CH3] respectively, in which the 2-deoxy substituent Z is azido, amino, propionamido, or acetamido, were prepared by chemical synthesis. Both types of modified trisaccharides are acceptors for a fucosyltransferase preparation obtained from human milk. Preparative fucosylations using this enzyme provided analogues of the sialyl Lewis(x) and sialyl Lewis(a) tetrasaccharide structures, which have been proposed to be ligands for cell-adhesion molecules. These syntheses further demonstrate the utility of glycosyltransferases in the preparation of oligosaccharide analogues.

MeSH terms

CA-19-9 Antigen
Carbohydrate Sequence
Fucosyltransferases*
Milk, Human / enzymology*
Molecular Sequence Data
Molecular Structure
Oligosaccharides / chemical synthesis*
Oxidation-Reduction
Sialyl Lewis X Antigen

Substances

CA-19-9 Antigen
Oligosaccharides
Sialyl Lewis X Antigen
Fucosyltransferases