Improved synthesis of an aldobiouronic acid related to hardwood xylans, and preparation of a derivative thereof suitable for linking to proteins

被引：18

作者：

Hirsch, J

Koós, M

Kovác, P ^{[1
]}

机构：

[1] NIDDK, NIH, Bethesda, MD 20892 USA

[2] Slovak Acad Sci, Inst Chem, SK-84238 Bratislava, Slovakia

来源：

CARBOHYDRATE RESEARCH | 1998年 / 310卷 / 1-2期

基金：

美国国家科学基金会;

关键词：

aldobiouronic acid; stereoselective alpha-glycosylation; xylopyranosides; disaccharides; neoglycoconjugate;

D O I：

10.1016/S0008-6215(98)00161-X

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：

Treatment of 1,3,4-tri-O-acetyl-alpha-D-xylopyranose with methyl 2,3-di-O-benzyl-1-chloro-1-deoxy-4-O-methyl-alpha, beta-D-glucopyranuronate in the presence of silver trifluoromethanesulfonate was highly stereoselective to give the alpha-linked aldobiouronic acid derivative (4) in 86% yield, after hydrogenolysis of the crude product of the coupling and chromatography. Compound 4 was acetylated and the fully protected substance was converted to the corresponding glycosyl chloride. Reaction of the latter with p-nitrophenol under phase-transfer catalysis afforded, after deacetylation, p-nitrophenyl 2-O-(methyl 4-O-methyl-alpha-D-glucopyranosyluronate)-beta-D-xylopyranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：145 / 149

页数：5

共 14 条

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TAKAHASHI N, 1990, WOOD RES, V77, P8

[12]

TIMELL TE, 1964, ADV CARBOHYD CHEM, V19, P247

[13] A CRYSTALLINE DERIVATIVE OF 2-O-(4-O-METHYL-ALPHA-D-GLUCOPYRANOSYLURONIC ACID)-D-XYLOPYRANOSE [J].