Asymmetric reduction of ethyl 2-methyl 3-oxobutanoate by fungi

被引:6
作者
Iwamoto, K
Kuramoto, T
Izumi, M
Kirihata, M
Dohmaru, T
Yoshizako, F
机构
[1] Univ Osaka Prefecture, Adv Sci & Technol Res Inst, Sakai, Osaka 5998570, Japan
[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
[3] Univ Osaka Prefecture, Coll Agr, Dept Appl Biochem, Sakai, Osaka 5998531, Japan
关键词
Penicillium purpurogenum; asymmetric reduction; ethyl; 2-methyl; 3-oxobutanoate; (2S; 3S)-ethyl; 3-hydroxybutanoate; 3R)-ethyl;
D O I
10.1271/bbb.64.194
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
Seven fungi, which are found to reduce ethyl 3-oxobutanoate in high yields, were tested for their reducing ability for ethyl 2-methyl 3-oxobutanoate. We obtained some interesting findings. In particular, Penicillium purpurogenum reduced ethyl 2-methyl 3-oxobutanoate to the corresponding alcohols with the diastereomer (anti/syn) ratio of 93/7 with the enantiomeric excess of anti-(2S,3S)- and syn-(2S,3R)-hydroxy esters of 90 and >99 ee%, respectively.
引用
收藏
页码:194 / 197
页数:4
相关论文
共 17 条
[1]  
Bingfeng Pan, 1995, Enzyme and Microbial Technology, V17, P853, DOI 10.1016/0141-0229(95)00004-O
[2]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICROBIOLOGICAL REDUCTION OF 2-METHYL 3-OXOALKANOATES [J].
BUISSON, D ;
SANNER, C ;
LARCHEVEQUE, M ;
AZERAD, R .
TETRAHEDRON LETTERS, 1987, 28 (34) :3939-3940
[3]  
Buisson D., 1990, BIOCATALYSIS, V3, P85
[4]   THE STEREOSELECTIVE ALPHA-ALKYLATION OF CHIRAL BETA-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF [J].
FRATER, G ;
MULLER, U ;
GUNTHER, W .
TETRAHEDRON, 1984, 40 (08) :1269-1277
[5]   YEAST CATALYZED REDUCTION OF BETA-KETO-ESTERS .1. FACTORS AFFECTING WHOLE-CELL CATALYTIC ACTIVITY AND STEREOSELECTIVITY [J].
HUNT, JR ;
CARTER, AS ;
MURRELL, JC ;
DALTON, H ;
HALLINAN, KO ;
CROUT, DHG ;
HOLT, RA ;
CROSBY, J .
BIOCATALYSIS AND BIOTRANSFORMATION, 1995, 12 (03) :159-178
[6]   Stereoselective reduction of alpha- and beta-keto esters with aerobic thermophiles, Bacillus strains [J].
Ishihara, K ;
Iwai, K ;
Yamaguchi, H ;
Nakajima, N ;
Nakamura, K ;
Ohshima, T .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1996, 60 (11) :1896-1898
[7]   Asymmetric reduction of ethyl 2-methyl 3-oxobutanoate by Chlorella [J].
Kuramoto, T ;
Iwamoto, K ;
Izumi, M ;
Kirihata, M ;
Yoshizako, F .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1999, 63 (03) :598-601
[8]  
MATSUMURA K, 1990, Patent No. 2138235
[9]   Stereoselective reduction of ethyl 2-methyl-3-oxobutanoate by bacteria [J].
Miya, H ;
Kawada, M ;
Sugiyama, Y .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1996, 60 (01) :95-98
[10]   DIASTEREOSELECTIVE AND ENANTIO-SELECTIVE REDUCTION OF 2-METHYL-3-OXOBUTANOATE BY BAKERS-YEAST [J].
NAKAMURA, K ;
MIYAI, T ;
NOZAKI, K ;
USHIO, K ;
OKA, S ;
OHNO, A .
TETRAHEDRON LETTERS, 1986, 27 (27) :3155-3156