Highly enantioselective reduction of carbonyl compounds using a reductase purified from bakers' yeast

被引:38
作者
Ema, T [1 ]
Sugiyama, Y [1 ]
Fukumoto, M [1 ]
Moriya, H [1 ]
Cui, JN [1 ]
Sakai, T [1 ]
Utaka, M [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 700, Japan
关键词
D O I
10.1021/jo980165e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An NADPH-dependent reductase that shows reducing activity for 1-chloro-2-hexanone has been purified from bakers' yeast. SDS-PAGE and gel filtration suggested that the purified reductase is a monomeric enzyme with a molecular weight of ca. 37 kDa. Asymmetric reduction of several carbonyl compounds using the purified reductase has been carried out. 1-Chloro-2-hexanone, 1-acetoxy-2-heptanone, methyl acetoacetate, ethyl pyruvate, 1-chloro-2,4-pentanedione, and 2,4-hexanedione were reduced to the corresponding alcohols with high enantiomeric purities (>98% ee). The reductase showed high specificity constants (k(cat)/K-m = 10(3)-10(5) s(-1) M-1) and relatively low Michaelis constants (K-m= 10(-4)-10(-3) M) for all the substrates examined.
引用
收藏
页码:4996 / 5000
页数:5
相关论文
共 41 条
[1]   The acylation of methyl ketones with aliphatic esters by means of sodium amide synthesis of beta-diketones of the type RCOCH2COR [J].
Adams, JT ;
Hauser, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1220-1222
[2]  
BARRY J, 1981, SYNTHESIS-STUTTGART, P453
[3]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[4]   LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS [J].
BRADSHAW, CW ;
HUMMEL, W ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1532-1536
[5]   THE USE OF AN ALTERED SPECIFICITY ENGINEERED ENZYME FOR ASYMMETRIC-SYNTHESIS - ENANTIOSELECTIVE REDUCTION OF 4-METHYL-2-OXOPENT-3-ENOIC ACID [J].
CASY, G ;
LEE, TV ;
LOVELL, H ;
NICHOLS, BJ ;
SESSIONS, RB ;
HOLBROOK, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (13) :924-926
[6]   STEREOSELECTIVE ROUTES TO CHIRAL 2-HYDROXY-4-OXO ACIDS AND SUBSTITUTED 2-HYDROXYBUTYROLACTONES USING LACTATE-DEHYDROGENASES [J].
CASY, G .
TETRAHEDRON LETTERS, 1992, 33 (52) :8159-8162
[7]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[8]   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
[9]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[10]   Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives [J].
Cui, JN ;
Teraoka, R ;
Ema, T ;
Sakai, T ;
Utaka, M .
TETRAHEDRON LETTERS, 1997, 38 (17) :3021-3024