A PSEUDOMONAS SP ALCOHOL-DEHYDROGENASE WITH BROAD SUBSTRATE-SPECIFICITY AND UNUSUAL STEREOSPECIFICITY FOR ORGANIC-SYNTHESIS

被引:110
作者
BRADSHAW, CW [1 ]
FU, H [1 ]
SHEN, GJ [1 ]
WONG, CH [1 ]
机构
[1] Scripps Res Inst, RES INST, DEPT CHEM, 10666 N TORREY PINES RD, LA JOLLA, CA 92037 USA
关键词
D O I
10.1021/jo00031a036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new alcohol dehydrogenase from Pseudomonas sp. strain PED has been isolated and characterized. The enzyme exhibits a broad substrate specificity, accepting aromatic, cyclic, and aliphatic compounds as substrates. The K(m) values were determined as 525-mu-M for NAD and 75-mu-M for 2-propanol with a specific activity of 36 U/mg. The kinetic mechanism is ordered bi-bi with the cofactor binding first and releasing last. The enzyme transfers the pro-R hydride of NADH to the si face of carbonyl compounds to yield (R) alcohols. Synthetic-scale reductions of a number of representative compounds were carried out in high enantiomeric excess with in situ regeneration of NADH using 2-propanol as the hydride source and the same enzyme as catalyst.
引用
收藏
页码:1526 / 1532
页数:7
相关论文
共 37 条
[21]   THERMOSTABLE ENZYMES IN ORGANIC-SYNTHESIS .2. ASYMMETRIC REDUCTION OF KETONES WITH ALCOHOL-DEHYDROGENASE FROM THERMOANAEROBIUM-BROCKII [J].
KEINAN, E ;
HAFELI, EK ;
SETH, KK ;
LAMED, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (01) :162-169
[22]   RESOLUTION OF RACEMIC MIXTURES VIA LIPASE CATALYSIS IN ORGANIC-SOLVENTS [J].
KIRCHNER, G ;
SCOLLAR, MP ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7072-7076
[23]  
KORNILOV AM, 1988, ZH ORG KHIM+, V24, P1343
[24]   ENZYME-CATALYZED ORGANIC-SYNTHESIS - A COMPARISON OF STRATEGIES FOR INSITU REGENERATION OF NAD FROM NADH [J].
LEE, LG ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :6999-7008
[25]  
LEMIERE GL, 1986, ENZYMES CATALYSTS OR, P19
[26]   KINETIC EVIDENCE FOR THE FORMATION OF DISCRETE 1,4-DEHYDROBENZENE INTERMEDIATES - TRAPPING BY INTERMOLECULAR AND INTRAMOLECULAR HYDROGEN-ATOM TRANSFER AND OBSERVATION OF HIGH-TEMPERATURE CIDNP [J].
LOCKHART, TP ;
COMITA, PB ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4082-4090
[27]  
MORI A, 1986, TETRAHEDRON, V42, P6447, DOI 10.1016/S0040-4020(01)88107-2
[28]   ABSOLUTE CONFIGURATION OF SUBSTITUTED TRIFLUOROMETHYLCARBINOLS [J].
PETERS, HM ;
FEIGL, DM ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4245-&
[29]  
Prelog V, 1964, PURE APPL CHEM, V9, P119
[30]   A NEW NAD-DEPENDENT ALCOHOL-DEHYDROGENASE WITH OPPOSITE FACIAL SELECTIVITY USEFUL FOR ASYMMETRIC REDUCTION AND COFACTOR REGENERATION [J].
SHEN, GJ ;
WANG, YF ;
BRADSHAW, C ;
WONG, CH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (09) :677-679