A facile synthesis of nitrophenyl oligosaccharides containing the O-alpha-L-fucopyranosyl-(1----3)-2-acetamido-2-deoxy-beta-D-glucopyrano syl unit at their nonreducing end

R K Jain; C F Piskorz; K L Matta

doi:10.1016/s0008-6215(00)90562-7

A facile synthesis of nitrophenyl oligosaccharides containing the O-alpha-L-fucopyranosyl-(1----3)-2-acetamido-2-deoxy-beta-D-glucopyrano syl unit at their nonreducing end

Carbohydr Res. 1992 Apr 10;228(1):243-53. doi: 10.1016/s0008-6215(00)90562-7.

Authors

R K Jain¹, C F Piskorz, K L Matta

Affiliation

¹ Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, New York 14263.

PMID: 1516089
DOI: 10.1016/s0008-6215(00)90562-7

Abstract

A facile approach towards the synthesis of 4-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-2-acetamido-2-deoxy-beta-D-glucopyra nos ide, 2-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D-glucop yra nosyl)- (1----6)-2-acetamido-2-deoxy-alpha-D-galactopyranoside, 4-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D-glucop yra nosyl)- (1----6)-alpha-D-mannopyranoside, and 4-nitrophenyl O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D-glucop yra nosyl)-(1----6)-beta-D-galactopyranoside has been accomplished through the development and use of methyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-beta-L-fucopyranoside as the glycosyl donor.

Publication types

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

MeSH terms

Antigens, Tumor-Associated, Carbohydrate / chemistry*
Carbohydrate Sequence
Molecular Sequence Data
Nitrophenols / chemistry*
Oligosaccharides / chemical synthesis*

Substances

Antigens, Tumor-Associated, Carbohydrate
Nitrophenols
Oligosaccharides