Expeditious synthesis of a trisubstrate analogue for alpha(1 -> 3) fucosyltransferase

被引：12

作者：

Heskamp, B. M. ^{[1
]}

van der Marel, G. A. ^{[1
]}

van Boom, J. H. ^{[1
]}

机构：

[1] Leiden Univ, Gorlaeus Labs, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1995年 / 14卷 / 09期

关键词：

D O I：

10.1080/07328309508005410

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of cyclohexyl 2-acetamido-2-deoxy-3-O-{2-O-[2-(guanosine 5'O-phosphate) ethyl]-alpha-L-fucopyranosyl}-beta- D-glucopyranoside (l), a potential inhibitor of alpha(1 -> 3) fucosyltransferases, is described. Target compound 1 was assembled via fucosylation of cyclohexyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside (6) with ethyl 2-O-[2-(benzoylhydroxy)ethyl]-3,4-O-isopropylidene-1-thio-beta-L- fucopyranoside (5) followed by debenzoylation, subsequent condensation of the resulting compound with 3 ',4'-di-0-benzoyl-5-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)-2-N-diphenylacetylguanosine (10) and deprotection.

引用

页码：1265 / 1277

页数：13

共 21 条

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