ENANTIOSELECTIVE REDUCTION OF BETA,GAMMA-UNSATURATED ALPHA-KETO ACIDS USING BACILLUS-STEAROTHERMOPHILUS LACTATE-DEHYDROGENASE - A NEW ROUTE TO FUNCTIONALIZED ALLYLIC ALCOHOLS

被引:26
作者
CASY, G [1 ]
LEE, TV [1 ]
LOVELL, H [1 ]
机构
[1] UNIV BRISTOL, CTR MOLEC RECOGNIT, BRISTOL BS8 1TS, AVON, ENGLAND
关键词
D O I
10.1016/S0040-4039(00)77723-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective reduction of alpha-keto acids, catalysed by lactate dehydrogenase, has been extended to beta,chi-unsaturated substrates, providing functionalised allylic alcohols in high optical purity.
引用
收藏
页码:817 / 820
页数:4
相关论文
共 16 条
[1]   CLONING, EXPRESSION AND COMPLETE NUCLEOTIDE-SEQUENCE OF THE BACILLUS-STEAROTHERMOPHILUS L-LACTATE DEHYDROGENASE GENE [J].
BARSTOW, DA ;
CLARKE, AR ;
CHIA, WN ;
WIGLEY, D ;
SHARMAN, AF ;
HOLBROOK, JJ ;
ATKINSON, T ;
MINTON, NP .
GENE, 1986, 46 (01) :47-55
[2]   ENZYMES IN ORGANIC-SYNTHESIS .45. AN EVALUATION OF THE SUBSTRATE-SPECIFICITY AND ASYMMETRIC-SYNTHESIS POTENTIAL OF THE CLONED L-LACTATE DEHYDROGENASE FROM BACILLUS-STEAROTHERMOPHILUS [J].
BUR, D ;
LUYTEN, MA ;
WYNN, H ;
PROVENCHER, LR ;
JONES, JB ;
GOLD, M ;
FRIESEN, JD ;
CLARKE, AR ;
HOLBROOK, JJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (06) :1065-1070
[3]   FROM ANALYSIS TO SYNTHESIS - NEW LIGAND-BINDING SITES ON THE LACTATE-DEHYDROGENASE FRAMEWORK .2. [J].
CLARKE, AR ;
ATKINSON, T ;
HOLBROOK, JJ .
TRENDS IN BIOCHEMICAL SCIENCES, 1989, 14 (04) :145-148
[4]   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-&
[5]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[6]   L-LACTATE DEHYDROGENASE - SUBSTRATE-SPECIFICITY AND USE AS A CATALYST IN THE SYNTHESIS OF HOMOCHIRAL 2-HYDROXY ACIDS [J].
KIM, MJ ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2959-2964
[7]   SYNTHESIS OF OPTICALLY PURE (R)-2-HYDROXY ACIDS USING D-LACTATE DEHYDROGENASE [J].
KIM, MJ ;
KIM, JY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) :326-327
[8]   STEREOSELECTIVE REDUCTION OF C=X BY A CHIRAL 1,4-DIHYDROPYRIDINE (NADH-MIMIC) IN A SELF-IMMOLATIVE PROCESS [J].
MEYERS, AI ;
BROWN, JD .
TETRAHEDRON LETTERS, 1988, 29 (44) :5617-5620
[9]   NAD(P)+-NAD(P)H MODELS .59. 1,2-REDUCTION VERSUS 1,4-REDUCTION OF BETA,GAMMA-UNSATURATED ALPHA-KETO ESTER [J].
OHNO, A ;
YASUMA, T ;
NAKAMURA, K ;
OKA, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (09) :2905-2906
[10]  
RAMBAUD M, 1988, SYNTHESIS-STUTTGART, P564