SYNTHESES OF 4'-DEOXY-ALPHA-MALTOSYL FLUORIDE AND 4''-DEOXY-ALPHA-MALTOTRIOSYL FLUORIDE AS PROBES OF ALPHA-GLUCANOTRANSFERASE MECHANISMS

被引：10

作者：

LINDHORST, TK ^{[1
]}

BRAUN, C ^{[1
]}

WITHERS, SG ^{[1
]}

机构：

[1] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER,BC V6T 1Z1,CANADA

来源：

CARBOHYDRATE RESEARCH | 1995年 / 268卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

4'-DEOXY-ALPHA-MALTOSYL FLUORIDE; 4''-DEOXY-ALPHA-MALTOTRIOSYL FLUORIDE; ENZYME PROBE; ALPHA-GLUCANOTRANSFERASE;

D O I：

10.1016/0008-6215(94)00317-9

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：

4'-Deoxy-alpha-maltosyl fluoride and 4''-deoxy-alpha-maltotriosyl fluoride were synthesized to serve as mechanistic probes for alpha-glucanotransferases such as the glycogen debranching enzyme. The deoxy derivatives were prepared starting from maltose and maltotriose, respectively. Deoxygenation of the terminal 4-hydroxyl group was accomplished by radical reduction of the iodo sugar formed after iodide displacement of the corresponding protected triflate. The anomeric fluoride was introduced by treatment of the protected hemiacetal with diethylaminosulfur trifluoride, predominantly giving the beta-anomeric product. Conversion to the alpha anomer was achieved using HF . pyridine.

引用

页码：93 / 106

页数：14

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