Selective oxidation of primary alcohol groups of β-cyclodextrin mediated by 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)

被引：72

作者：

Fraschini, C ^{[1
]}

Vignon, MR ^{[1
]}

机构：

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

来源：

CARBOHYDRATE RESEARCH | 2000年 / 328卷 / 04期

关键词：

TEMPO oxidation; beta-cyclodextrin; primary alcohol oxidation; 6-carboxy-beta-cyclodextrins; H-1 and C-13 NMR;

D O I：

10.1016/S0008-6215(00)00129-4

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：

beta-Cyclodextrin (beta-CD) was reacted with catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO), sodium hypochlorite and sodium bromide at 2 degrees C and a pH value of 10 in water. The primary alcohol groups were selectively oxidized into carboxylate groups within a few minutes, and mono- and dicarboxy-beta-cyclodextrin sodium salts were isolated and characterized by H-1, C-13 NMR and mass spectroscopy. With this reaction system, the degradation of the cyclodextrin was limited, provided the oxidation was performed at 2 degrees C, at constant pH value of 10, with catalytic amounts of TEMPO and controlled quantities of sodium hypochlorite and sodium bromide for the continuous regeneration of the oxoammonium salt. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：585 / 589

页数：5

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