LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS

被引:197
作者
BRADSHAW, CW
HUMMEL, W
WONG, CH
机构
[1] Scripps Res Inst, RES INST, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA
[2] UNIV DUSSELDORF, INST ENZYMTECHNOL, W-4000 DUSSELDORF 1, GERMANY
[3] FORSCHUNGSZENTRUM JULICH, FORSCHUNGSZENTRUM JULICH, W-5170 JULICH 1, GERMANY
关键词
D O I
10.1021/jo00031a037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alcohol dehydrogenase from Lactobacillus kefir simultaneously catalyzes carbonyl reductions and NADPH regeneration in the presence of 2-propanol. Representative synthesis of a number of chiral alcohols was accomplished in good yield and high enantiomeric excess (94-99%). This NADPH-requiring enzyme transfers the pro-R hydride from the cofactor to the si face of carbonyls to give (R) alcohols. The enzyme exhibits a very broad substrate specificity and high enantioselectivity for the synthesis of chiral aromatic, cyclic, polycyclic, and aliphatic alcohols.
引用
收藏
页码:1532 / 1536
页数:5
相关论文
共 30 条
[1]   DETERMINATION OF HYDRIDE TRANSFER STEREOSPECIFICITY OF NICOTINAMIDE ADENINE-DINUCLEOTIDE LINKED OXIDOREDUCTASES BY PROTON MAGNETIC-RESONANCE [J].
ARNOLD, LJ ;
YOU, K ;
ALLISON, WS ;
KAPLAN, NO .
BIOCHEMISTRY, 1976, 15 (22) :4844-4849
[2]   SILYL DERIVATIVES OF PYRAZOLE, ISOXAZOLE AND 1,2,3-TRIAZOLE [J].
BIRKOFER, L ;
RICHTZENHAIN, K .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08) :2829-2836
[3]  
BIRKOFER L, 1987, CHEM BER, V120, P1059
[4]  
BRADSHAW CW, IN PRESS BIOORG CHEM
[5]  
BRADSHAW CW, 1992, J ORG CHEM, V57
[6]   ASYMMETRIC REDUCTION - REDUCTION OF ACETYLENIC KETONES WITH CHIRAL HYDRIDE AGENT [J].
BRINKMEYER, RS ;
KAPOOR, VM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8339-8341
[7]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[8]   REGENERATION OF NICOTINAMIDE COFACTORS FOR USE IN ORGANIC-SYNTHESIS [J].
CHENAULT, HK ;
WHITESIDES, GM .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 1987, 14 (02) :147-197
[9]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[10]   CHEMOENZYMIC SYNTHESIS OF CHIRAL FURAN-DERIVATIVES - USEFUL BUILDING-BLOCKS FOR OPTICALLY-ACTIVE STRUCTURES [J].
DRUECKHAMMER, DG ;
BARBAS, CF ;
NOZAKI, K ;
WONG, CH ;
WOOD, CY ;
CIUFOLINI, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1607-1611