SYNTHESIS OF D-BIOTIN CHIRAL INTERMEDIATES VIA A BIOCHEMICAL METHOD

被引:10
作者
YAMANO, T
TOKUYAMA, S
AOKI, I
NISHIGUCHI, Y
NAKAHAMA, K
TAKANOHASHI, K
机构
关键词
D O I
10.1246/bcsj.66.1456
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enzyme-catalyzed kinetic resolution of (+/-)-(3aalpha,4alpha,6aalpha)-4-acetoxy-1,3-dibenzyl-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one [(RS)-(3a)] was examined. Lipase B from Pseudomonas fragi and rabbit liver esterase gave (-)-[3aR-(3aalpha,4alpha,6aalpha)]-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno[3,4-Aimidazol-2(3H)-one [(R)-(2)], while Streptomyces rochei var. volubilis gave the alcohol (S)-(2), which is a key intermediate in the synthesis of d-biotin, with high enantioselectivity.
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页码:1456 / 1460
页数:5
相关论文
共 15 条
[1]   NUCLEOPHILIC DISPLACEMENTS ON AN ALPHA-CHLORO THIOETHER BY ORGANOCUPRATES - A NOVEL SYNTHESIS OF DESOXYBIOTIN [J].
BATES, HA ;
ROSENBLUM, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3447-3451
[2]   SYNTHESIS OF (+)-BIOTIN - EFFICIENT RESOLUTION OF KEY INTERMEDIATES [J].
BIHOVSKY, R ;
BODEPUDI, V .
TETRAHEDRON, 1990, 46 (23) :7667-7676
[3]   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
[4]   A SIMPLE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-BIOTIN [J].
COREY, EJ ;
MEHROTRA, MM .
TETRAHEDRON LETTERS, 1988, 29 (01) :57-60
[5]  
GOLDBERG MW, 1949, Patent No. 2489234
[6]  
GOLDBERG MW, 1949, Patent No. 2489232
[7]  
GOLDBERG MW, 1949, Patent No. 2489235
[8]  
HIGASHIDE E, 1971, J ANTIBIOT, V24, P1
[9]   ASYMMETRIC HYDROLYSIS OF ESTERS BY BIOCHEMICAL METHODS .5. ASYMMETRIC HYDROLYSIS OF PROCHIRAL DIESTERS WITH PIG-LIVER ESTERASE - PREPARATION OF OPTICALLY-ACTIVE INTERMEDIATES FOR THE SYNTHESIS OF (+)-BIOTIN AND (+)-ALPHA-METHYL-3,4-DIHYDROXYPHENYLALANINE [J].
IRIUCHIJIMA, S ;
HASEGAWA, K ;
TSUCHIHASHI, G .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (07) :1907-1910
[10]   A RULE TO PREDICT WHICH ENANTIOMER OF A SECONDARY ALCOHOL REACTS FASTER IN REACTIONS CATALYZED BY CHOLESTEROL ESTERASE, LIPASE FROM PSEUDOMONAS-CEPACIA, AND LIPASE FROM CANDIDA-RUGOSA [J].
KAZLAUSKAS, RJ ;
WEISSFLOCH, ANE ;
RAPPAPORT, AT ;
CUCCIA, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2656-2665