PREASSOCIATING ALPHA-NUCLEOPHILES BASED ON BETA-CYCLODEXTRIN - THEIR SYNTHESIS AND REACTIVITY

被引：25

作者：

MARTIN, KA ^{[1
]}

MORTELLARO, MA ^{[1
]}

SWEGER, RW ^{[1
]}

FIKES, LE ^{[1
]}

WINN, DT ^{[1
]}

CLARY, S ^{[1
]}

JOHNSON, MP ^{[1
]}

CZARNIK, AW ^{[1
]}

机构：

[1] OHIO STATE UNIV, DEPT CHEM, COLUMBUS, OH 43210 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 42期

关键词：

D O I：

10.1021/ja00147a005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methods are reported for the attachment of alpha-nucleophiles to the primary and secondary sides of the cyclodextrin cavity. Six new materials have been prepared in which beta CD has been modified by hydrazine, hydroxylamine, oxime, and hydroperoxide functionalities. Transacylating studies with p-NPA have demonstrated that the primary-side hydroxylamine shows the highest reactivity with a 1900-fold increase in rate over beta CD at pH 6.5. Other alpha-nucleophiles show less remarkable rate increases in this system but, in some cases, demonstrate hydrogen-bonding to the cyclodextrin rim and inhibition kinetics.

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收藏

页码：10443 / 10448

页数：6

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