THE EFFECT OF ARYL FLUORINES IN A LIPASE RESOLUTION

被引:8
作者
DASARADHI, L [1 ]
OHAGAN, D [1 ]
机构
[1] UNIV DURHAM,DEPT CHEM,SCI LABS,SOUTH RD,DURHAM DH1 3LE,ENGLAND
关键词
D O I
10.1016/S0960-894X(00)80036-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The steric influence of fluorine compared to hydrogen in enzymatic systems is probed by the resolution of a series of fluorinated benzhydrol acetates with lipases. Lipase AY-Amano-30 from Candida cylindracea can distinguish a single fluorine atom and the discrimination is most significant with fluorine in the ortho position close to the reaction centre. Increasing the number of fluorine atoms improves the discrimination and 2,3,4,5,6-pentafluoroaryl benzhydrol was resolved in 86%ee after 35% conversion.
引用
收藏
页码:1655 / 1658
页数:4
相关论文
共 10 条
[1]  
ANH NT, 1977, NOUV J CHIM, V1, P61
[2]  
BERGMANN ED, 1961, B RES COUNC ISRAEL, VA 10, P1
[3]   THEORY AND MODELING OF STEREOSELECTIVE ORGANIC-REACTIONS [J].
HOUK, KN ;
PADDONROW, MN ;
RONDAN, NG ;
WU, YD ;
BROWN, FK ;
SPELLMEYER, DC ;
METZ, JT ;
LI, Y ;
LONCHARICH, RJ .
SCIENCE, 1986, 231 (4742) :1108-1117
[4]   KINETIC RESOLUTION OF 2-SUBSTITUTED ESTERS CATALYZED BY A LIPASE EX PSEUDOMONAS-FLUORESCENS [J].
KALARITIS, P ;
REGENYE, RW ;
PARTRIDGE, JJ ;
COFFEN, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :812-815
[5]   SYNTHESIS OF THE OPTICALLY PURE MONOETHYL ESTER OF (R)-(+)-2-FLUOROMALONIC ACID BY USE OF IMMOBILIZED LIPASE-MY FOR ASYMMETRIC HYDROLYSIS [J].
KITAZUME, T ;
MURATA, K ;
IKEYA, T .
JOURNAL OF FLUORINE CHEMISTRY, 1986, 31 (02) :143-150
[6]  
MANN J, 1987, CHEM SOC REV, V16, P361
[7]   ORGANIC-SYNTHESIS - WHERE NOW [J].
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1990, 29 (11) :1320-1367
[8]  
WALSH C, 1982, ADV ENZYMOL, V55, P197
[9]   ADVANCES IN THE PREPARATION OF BIOLOGICALLY-ACTIVE ORGANOFLUORINE COMPOUNDS [J].
WELCH, JT .
TETRAHEDRON, 1987, 43 (14) :3123-3197
[10]   THEORETICAL EVIDENCE IN SUPPORT OF THE ANH-EISENSTEIN ELECTRONIC MODEL IN CONTROLLING PI-FACIAL STEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CARBONYL-COMPOUNDS [J].
WONG, SS ;
PADDONROW, MN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :456-458