Synthesis of allyl 2-O-(α-L-arabinofuranosyl)-6-O-(α-D-mannopyranosyl)-β-D-mannopyranoside, a unique plant N-glycan motif containing arabinose

被引：17

作者：

Utille, JP ^{[1
]}

Priem, B ^{[1
]}

机构：

[1] Univ Grenoble 1, Ctr Rech Macromol Vegetales, CNRS, UPR 5301, F-38041 Grenoble, France

来源：

CARBOHYDRATE RESEARCH | 2000年 / 329卷 / 02期

关键词：

L-arabinose; plant N-glycan; beta-D-allyl mannoside;

D O I：

10.1016/S0008-6215(00)00185-3

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 the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：431 / 439

页数：9

共 16 条

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OTTOSSON, H
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HANSMANN, CF
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Borbás, A
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Boger, D.L.
Honda, T.
Journal of the American Chemical Society, 1994, 116 (13):
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Crich, David
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CARBOHYDRATE RESEARCH, 2009, 344 (01) : 140 - 144
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ZAMYATINA, AY
SHVETS, VI
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[8] SYNTHESIS AND EVALUATION OF THE FULLY FUNCTIONALIZED BLEOMYCIN A(2) METAL-BINDING DOMAIN-CONTAINING THE 2-O-(3-O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-ALPHA-L-GULOPYRANOSYL DISACCHARIDE
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Ledvina, M., 1600, (251):

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