Asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol using acetone powder of Geotrichum candidum

被引:29
作者
Hamada, H
Miura, T
Kumobayashi, H
Matsuda, T
Harada, T
Nakamura, K
机构
[1] Okayama Univ Sci, Dept Appl Sci, Okayama 7000005, Japan
[2] Takasago Int Corp, Hiratsuka, Kanagawa 2540073, Japan
[3] Ryukoku Univ, Fac Sci & Technol, Dept Chem Mat, Shiga 5202194, Japan
[4] Kyoto Univ, Chem Res Inst, Kyoto 6110011, Japan
关键词
biotransformation; chiral alcohols; enantioselective reduction; Geotrichum candidum;
D O I
10.1023/A:1011922823367
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
The asymmetric synthesis of (R)-2-chloro-1-(m-chlorophenyl)ethanol, a precursor for a key intermediate of an important class of drugs, was achieved by reduction of the corresponding ketone using an acetone powder of Geotrichum candidum with 98% ee and 94% yield based on the starting amount of ketone.
引用
收藏
页码:1603 / 1606
页数:4
相关论文
共 12 条
[1]   SYNTHESIS OF THE POTENT AND SELECTIVE ATYPICAL BETA-ADRENERGIC AGONIST SR 59062A [J].
BADONE, D ;
GUZZI, U .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) :1921-1924
[2]   DISODIUM (R,R)-5-[2-[[2-(3-CHLOROPHENYL)-2-HYDROXYETHYL]AMINO]PROPYL]-1,3-BENZODIOXOLE-2,2-DICARBOXYLATE (CL 316,243) - A POTENT BETA-ADRENERGIC AGONIST VIRTUALLY SPECIFIC FOR BETA-3 RECEPTORS - A PROMISING ANTIDIABETIC AND ANTIOBESITY AGENT [J].
BLOOM, JD ;
DUTIA, MD ;
JOHNSON, BD ;
WISSNER, A ;
BURNS, MG ;
LARGIS, EE ;
DOLAN, JA ;
CLAUS, TH .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) :3081-3084
[3]   Production of chiral alcohols by enantioselective reduction with NADH-dependent phenylacetaldehyde reductase from Corynebacterium strain, ST-10 [J].
Itoh, N ;
Mizuguchi, N ;
Mabuchi, M .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1999, 6 (1-2) :41-50
[4]   MICROBIAL-PRODUCTION OF CHIRAL PANTOTHENONITRILE THROUGH STEREOSPECIFIC REDUCTION OF 2'-KETOPANTOTHENONITRILE [J].
KATAOKA, M ;
SHIMIZU, S ;
DOI, Y ;
SAKAMOTO, K ;
YAMADA, H .
BIOTECHNOLOGY LETTERS, 1990, 12 (05) :357-360
[5]   Two classes of enzymes of opposite stereochemistry in an organism: One for fluorinated and another for nonfluorinated substrates [J].
Matsuda, T ;
Harada, T ;
Nakajima, N ;
Itoh, T ;
Nakamura, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :157-163
[6]   Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum [J].
Nakamura, K ;
Matsuda, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8957-8964
[7]   DIASTEREO-SELECTIVE AND ENANTIO-SELECTIVE REDUCTION OF ETHYL 2-METHYL-3-OXOBUTANOATE BY PLANT-CELL CULTURES [J].
NAKAMURA, K ;
MIYOSHI, H ;
SUGIYAMA, T ;
HAMADA, H .
PHYTOCHEMISTRY, 1995, 40 (05) :1419-1420
[8]   ENZYMATIC CATALYSIS IN A SUPERCRITICAL FLUID [J].
RANDOLPH, TW ;
BLANCH, HW ;
PRAUSNITZ, JM ;
WILKE, CR .
BIOTECHNOLOGY LETTERS, 1985, 7 (05) :325-328
[9]   ENANTIOSELECTIVE CATALYTIC REDUCTIONS OF KETONES WITH NEW 4 MEMBERED OXAZABOROLIDINES - APPLICATION TO (S)-TETRAMISOLE [J].
RAO, AVR ;
GURJAR, MK ;
KAIWAR, V .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :859-862
[10]   BIOTRANSFORMATION OF EXOGENOUS SUBSTRATES BY PLANT-CELL CULTURES [J].
SUGA, T ;
HIRATA, T .
PHYTOCHEMISTRY, 1990, 29 (08) :2393-2406