BIOTRANSFORMATIONS USING CLOSTRIDIA - STEREOSPECIFIC REDUCTIONS OF A BETA-KETO ESTER

被引:5
|
作者
CHRISTEN, M
CROUT, DHG
HOLT, RA
MORRIS, JG
SIMON, H
机构
[1] UNIV COLL WALES ABERYSTWYTH,DEPT BIOL SCI,ABERYSTWYTH SY23 3DA,DYFED,WALES
[2] TECH UNIV MUNICH,INST ORGAN CHEM,W-8046 GARCHING,GERMANY
关键词
D O I
10.1039/p19920000491
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reduction of methyl 4-(4-chlorophenylthio)-3-oxobutanoate 1 by clostridia has been studied. Clostridium pasteurianum ATCC 6013, C. tyrobutyricum DSM 1460 and C. kluyveri NCIB 10680 gave the D-(3S) reduction product 2, whereas C. kluyveri DSM 555 gave the L-(3R) reduction product 3. The products could be obtained in higher optical purities than by yeast reductions.
引用
收藏
页码:491 / 493
页数:3
相关论文
共 50 条
  • [1] STEREOCHEMISTRY OF BETA-KETO ESTER AND BETA-KETO NITRILE ALKYLATIONS
    KUEHNE, ME
    JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (01): : 171 - &
  • [2] DIASTEREOSELECTIVE REDUCTIONS OF BETA-KETO SULFOXIMINES
    JOHNSON, CR
    STARK, CJ
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07): : 1196 - 1200
  • [3] ACYLATION OF BETA-KETO ESTER DIANIONS
    HUCKIN, SN
    WEILER, L
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (08): : 1343 - 1351
  • [4] VERSATILE BETA-KETO ESTER AND BETA-KETO NITRILE SYNTHESIS THROUGH SULFIDE CONTRACTION
    SHIOSAKI, K
    FELS, G
    RAPOPORT, H
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16): : 3230 - 3234
  • [5] CHIRALITY AS A PROBE IN BETA-KETO ESTER TAUTOMERISM
    DECICCO, CP
    BUCKLE, RN
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03): : 1005 - 1008
  • [6] ELECTROPHILIC CYCLIZATION OF AN OLEFINIC BETA-KETO ESTER
    ALDERDICE, M
    WEILER, L
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (14): : 2239 - 2241
  • [7] SOME TETRAHYDROTHIOPHENE BETA-KETO ESTER DERIVATIVES
    CHENEY, LC
    PIENING, JR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (12) : 2213 - 2216
  • [8] STEREOCHEMISTRY OF REDUCTION OF BETA-KETO ESTERS, BETA-KETO AMIDES AND BETA-KETO NITRILES BY HYDRIDES
    CANCEILL, J
    JACQUES, J
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, (06): : 2180 - &
  • [9] RING FORMATION VIA BETA-KETO ESTER DIANIONS
    SUM, PE
    WEILER, L
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (06): : 996 - 1000
  • [10] ALDOL TYPE CONDENSATIONS OF BETA-KETO ESTER DIANIONS
    HUCKIN, SN
    WEILER, L
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (11): : 2157 - 2164