INTRODUCTION OF PLURAL ASYMMETRIC CENTERS BY A BETA-KETO ESTER REDUCTASE FROM BAKERS-YEAST

被引:11
作者
KAWAI, Y
HIDA, K
NAKAMURA, K
OHNO, A
机构
[1] Institute for Chemical Research, Kyoto University, Uji, Kyoto
关键词
D O I
10.1016/0040-4039(94)02260-I
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A beta-keto ester reductase from baker's yeast catalyzes asymmetric reduction accompanied by simultaneous kinetic resolution of dynamic and static optically active centers. The reduction of 1'-arylethyl 2-methyl-3-oxobutanoates mediated by this enzyme affords the corresponding (1'R)-1'-arylethyl (2R,3S)-3-hydroxy-2-methylbutanoates with excellent stereoselectivity.
引用
收藏
页码:591 / 592
页数:2
相关论文
共 12 条
[1]  
CERVINKA O, 1966, COLLECT CZECH CHEM C, V31, P2615
[2]   STEREOSELECTIVE REDUCTION OF PROCHIRAL KETONES, USING ALUMINUM-HYDRIDE REAGENTS PREPARED FROM LIALH4 AND CHIRAL DIETHANOLAMINES [J].
DEVRIES, EFJ ;
BRUSSEE, J ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :377-386
[3]   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
[4]   YEAST-MEDIATED RESOLUTION OF BETA-KETO-ESTERS OF PROCHIRAL ALCOHOLS [J].
HUDLICKY, T ;
TSUNODA, T ;
GADAMASETTI, KG ;
MURRY, JA ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3619-3623
[5]   DEHYDROGENASES FOR THE SYNTHESIS OF CHIRAL COMPOUNDS [J].
HUMMEL, W ;
KULA, MR .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1989, 184 (01) :1-13
[6]   ASYMMETRIC REDUCTION OF BETA-KETO-ESTERS WITH AN ENZYME FROM BAKERS-YEAST [J].
KAWAI, Y ;
TSUJIMOTO, M ;
KONDO, S ;
TAKANOBE, K ;
NAKAMURA, K ;
OHNO, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (02) :524-528
[7]   QUANTITATIVE EXPRESSION OF DYNAMIC KINETIC RESOLUTION OF CHIRALLY LABILE ENANTIOMERS - STEREOSELECTIVE HYDROGENATION OF 2-SUBSTITUTED 3-OXO CARBOXYLIC ESTERS CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES [J].
KITAMURA, M ;
TOKUNAGA, M ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :144-152
[8]   STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .14. STEREOSELECTIVE SYNTHESIS OF (2R,3S)-SYN-2-ALLYL-3-HYDROXY BUTANOATE MEDIATED BY AN ENZYMATIC SYSTEM FROM BAKERS-YEAST [J].
NAKAMURA, K ;
MIYAI, T ;
KAWAI, Y ;
NAKAJIMA, N ;
OHNO, A .
TETRAHEDRON LETTERS, 1990, 31 (08) :1159-1160
[9]   STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .9. DIASTEREOSELECTIVE REDUCTION OF 2-ALKYL-3-OXOBUTANOATE WITH BAKERS-YEAST [J].
NAKAMURA, K ;
MIYAI, T ;
NAGAR, A ;
OKA, S ;
OHNO, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (04) :1179-1187
[10]   STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .18. MECHANISM OF STEREOCHEMICAL CONTROL IN THE DIASTEREOSELECTIVE REDUCTION WITH BAKERS-YEAST [J].
NAKAMURA, K ;
KAWAI, Y ;
MIYAI, T ;
HONDA, S ;
NAKAJIMA, N ;
OHNO, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (05) :1467-1470