Resolution of non-protein amino acids via microbial protease-catalyzed ester hydrolysis: Marked enhancement of enantioselectivity by the use of esters with longer alkyl chains and at low temperature

被引:38
作者
Miyazawa, T
Minowa, H
Miyamoto, T
Imagawa, K
Yanagihara, R
Yamada, T
机构
[1] Department of Chemistry, Faculty of Science, Konan University, Kobe 658, Higashinada-ku
关键词
D O I
10.1016/S0957-4166(97)00002-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In the microbial protease-catalyzed hydrolysis of amino acid esters with the free alpha-amino group, the enantioselectivity can be enhanced greatly by employing esters with longer alkyl chains such as the isobutyl ester instead of the conventional methyl ester and by conducting the reaction at low temperature. (C) 1997 Elsevier Science Ltd. All rights reserved.
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页码:367 / 370
页数:4
相关论文
共 19 条
[1]   LIPASE CATALYZED REGIOSELECTIVE AND ENANTIOSELECTIVE HYDROLYSIS - MOLECULAR RECOGNITION PHENOMENON AND SYNTHESIS OF (R)-DIMORPHECOLIC ACID [J].
BHALERAO, UT ;
DASARADHI, L ;
NEELAKANTAN, P ;
FADNAVIS, NW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1197-1198
[2]   ENZYMATIC-HYDROLYSIS OF ALKYL 3,4-EPOXYBUTYRATES - A NEW ROUTE TO (R)-(-)-CARNITINE CHLORIDE [J].
BIANCHI, D ;
CABRI, W ;
CESTI, P ;
FRANCALANCI, F ;
RICCI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :104-107
[3]   CONTROL OF THE STEREOSELECTIVITY OF PIG-LIVER ESTERASE BY DIFFERENT REACTION CONDITIONS IN THE HYDROLYSIS OF CIS-N-BENZYL-2,5-BISMETHOXYCARBONYLPYRROLIDINE AND STRUCTURALLY RELATED DIESTERS [J].
BOUTELJE, J ;
HJALMARSSON, M ;
HULT, K ;
LINDBACK, M ;
NORIN, T .
BIOORGANIC CHEMISTRY, 1988, 16 (04) :364-375
[4]   HERSTELLUNG VON ALPHA-AMINOSAUREESTERN DURCH ALKOHOLYSE DER METHYLESTER [J].
BRENNER, M ;
HUBER, W .
HELVETICA CHIMICA ACTA, 1953, 36 (05) :1109-1115
[5]   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
[6]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[7]   CHEMOENZYMATIC PREPARATION OF ATROLACTIC AND MOSHERS ACID USING ASPERGILLUS-ORYZAE PROTEASE [J].
FEICHTER, C ;
FABER, K ;
GRIENGL, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :653-654
[8]  
FULLING G, 1987, J AM CHEM SOC, V109, P2845
[9]   TEMPERATURE AS AN ENANTIOSELECTIVE PARAMETER IN ENZYMATIC RESOLUTIONS OF RACEMIC MIXTURES [J].
HOLMBERG, E ;
HULT, K .
BIOTECHNOLOGY LETTERS, 1991, 13 (05) :323-326
[10]   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