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Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Le(x), Le(a), sialyl-Le(x) and sialyl-Le(a) epitopes recognized by selectins.

Abstract：

:A systematic synthesis of the N-methyl-1-deoxynojirimycin-containing oligosaccharides related to the Lewis x, Lewis a, sialyl-Lewis x and sialyl-Lewis a antigens has been achieved. The couplings of the suitably protected 1-deoxynojirimycin derivative 10 with methyl-1-thioglycosides (glycosyl donors) of L-fucose (11), D-galactose (15) and alpha-sialyl-(2-->3)-D-galactose (27) were carried out by using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) as the glycosyl promoter. The resulting di- and tri-saccharides were each converted, by further cross glycosylations with 11, 15 or 27, to the desired tri- and tetra-saccharides 3-6 that inhibit the recognition between sialyl-Lewis x and selectins, a family of leukocyte cell adhesion molecules.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Kiso M,Furui H,Ando K,Ishida H,Hasegawa A

doi

10.1016/s0968-0896(00)82080-5

subject

Has Abstract

pub_date

1994-11-01 00:00:00

pages

1295-308

issue

11

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(00)82080-5

journal_volume

2

pub_type

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