SYNTHESIS OF ESTER DERIVATIVES OF CHLORAMPHENICOL BY LIPASE-CATALYZED TRANSESTERIFICATION IN ORGANIC-SOLVENTS

被引:45
作者
OTTOLINA, G [1 ]
CARREA, G [1 ]
RIVA, S [1 ]
机构
[1] CNR,IST CHIM ORMONI,VIA MARIO BIANCO 9,I-20133 MILAN,ITALY
关键词
D O I
10.1021/jo00295a025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective esterification of chloramphenicol (1) and its synthetic analogue thiamphenicol (2) has been achieved bythe action of lipase in acetone and several methyl carboxylates. Aliphatic and aromatic esters of different sizes and natures have been introduced selectively on the primary hydroxyl group of these molecules by modification of the reaction conditions (e.g., temperature, solvent, and lipase source). © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:2366 / 2369
页数:4
相关论文
共 23 条
[1]   ENZYMATIC-SYNTHESIS OF VARIOUS 1'-O-SUCROSE AND 1-O-FRUCTOSE ESTERS [J].
CARREA, G ;
RIVA, S ;
SECUNDO, F ;
DANIELI, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1057-1061
[2]  
CERIOTTI G, 1954, Farmaco Sci, V9, P21
[3]   PREPARATIVE REGIOSELECTIVE ACYLATION OF GLYCOLS BY ENZYMATIC TRANSESTERIFICATION IN ORGANIC-SOLVENTS [J].
CESTI, P ;
ZAKS, A ;
KLIBANOV, AM .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 1985, 11 (05) :401-407
[4]  
CHENEVERT R, 1989, SYNTHESIS-STUTTGART, P444
[5]  
EDGERTON WH, 1954, CHEM ABSTR 12793E, V48
[6]  
EDGERTON WH, 1957, CHEM ABSTR 10575G, V51
[7]   BIOTRANSFORMATION OF ANTIBIOTICS .1. ACYLATION OF CHLORAMPHENICOL BY SPORES OF STREPTOMYCES-GRISEUS ISOLATED FROM EGYPTIAN SOIL [J].
ELKERSH, TA ;
PLOURDE, JR .
JOURNAL OF ANTIBIOTICS, 1976, 29 (03) :292-302
[8]  
GLAZER G, 1961, CHEM ABSTR 14387F, V55
[9]  
GOEBEL MT, 1959, CHEM ABSTR 1650I, V53
[10]  
HANROTH F, 1966, CHEM ABSTR 17483D, V64