SYNTHESIS OF 4'-DEOXY-4'-FLUOROKANAMYCIN-A AND 4'-DEOXY-4'-FLUOROKANAMYCIN-B

被引：12

作者：

TAKAHASHI, Y ^{[1
]}

TSUNEDA, S ^{[1
]}

TSUCHIYA, T ^{[1
]}

KOYAMA, Y ^{[1
]}

UMEZAWA, S ^{[1
]}

机构：

[1] INST BIOORGAN CHEM,1614 IDA,NAKAHARA KU,KAWASAKI 211,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1992年 / 232卷 / 01期

关键词：

D O I：

10.1016/S0008-6215(00)90996-0

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-4'-fluorokanamycins A (17) and B (25) have been prepared through fluorinative ring-opening of the D-galacto-3',4'-oxiranes (8 and 21) derived from kanamycin A and B with potassium hydrogenfluoride in ethane-1,2-diol. The mechanism of preponderant formation of the 4'-deoxy-4'-fluoro-D-gluco (9 and 22) over the 3'-deoxy-3'-fluoro-D-gulo derivatives was discussed. In the synthesis of 25, the unusual 3',6'-epimine (23) was the main product along with the 4'-deoxy-4'-fluoro derivative. The mechanism of this reaction is also discussed. Both 17 and 25 were active against resistant bacteria producing aminoglycoside-adenylylating enzymes for HO-4'.

引用

页码：89 / 105

页数：17

共 13 条

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