Synthesis of oxidized methyl 4-O-methyl-β-D-glucopyranoside and methyl β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside derivatives as substrates for fluorescence labeling reactions

被引：20

作者：

Röhrling, J ^{[1
]}

Potthast, A ^{[1
]}

Lange, T ^{[1
]}

Rosenau, T ^{[1
]}

Adorjan, I ^{[1
]}

Hofinger, A ^{[1
]}

Kosma, P ^{[1
]}

机构：

[1] Univ Agr Sci, Inst Chem, Christian Doppler Lab, A-1190 Vienna, Austria

来源：

CARBOHYDRATE RESEARCH | 2002年 / 337卷 / 08期

关键词：

oxidation; cellulose; cellobioside; fluorescence labelling;

D O I：

10.1016/S0008-6215(02)00048-4

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 synthetic cellulose model compounds methyl 4-O-methyl-beta-D-glucopyranoside and methyl 4-O-methyl-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside and related 6-O-protected intermediates were oxidized in good to fair yields using Swern-conditions or bromine/bis(tributyltin) oxide, respectively, to afford compounds containing 6-aldehyde, 3-keto, and 2,3-diketo groups. Cellobiose and oxidized monosaccharides were then labeled with the carbonyl-selective fluorescence marker 9-(7-amino-1,4,7-trioxaheptyl)-9H-carbazolecarboxamide (CCOA). The labeled derivatives serve as model compounds for the determination of minute amounts of carbonyl groups in cellulosic polysaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：691 / 700

页数：10

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