PREPARATION OF OPTICALLY-ACTIVE CYCLOHEXANEDIOLS AND (+)-ALPHA-HYDROXYCYCLOHEPTANONE BY AN ENZYME-CATALYZED STEREOINVERSION/OXIDATION PROCESS

被引:23
作者
CARNELL, AJ [1 ]
IACAZIO, G [1 ]
ROBERTS, SM [1 ]
WILLETTS, AJ [1 ]
机构
[1] UNIV EXETER,DEPT BIOL SCI,EXETER EX4 4QG,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)76545-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-trans and cis Cyclohexane-1,2-diols have been shown to undergo a double stereoinversion process to give trans (S,S)-cyclohexane-1,2-diols on incubation with the fungus C. cassiicola.
引用
收藏
页码:331 / 334
页数:4
相关论文
共 11 条
  • [1] HETEROGENEOUS PERMANGANATE OXIDATIONS - AN IMPROVED PROCEDURE FOR THE DIRECT CONVERSION OF OLEFINS TO ALPHA-DIKETONES ALPHA-HYDROXY KETONES
    BASKARAN, S
    DAS, J
    CHANDRASEKARAN, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) : 5182 - 5184
  • [2] CARON G, 1991, J ORG CHEM, V56, P725
  • [3] APPLICATIONS OF VIBRATIONAL INFRARED CIRCULAR-DICHROISM TO BIOLOGICAL PROBLEMS - STEREOCHEMISTRY OF PROTON-EXCHANGE IN ACETOIN (3-HYDROXYBUTAN-2-ONE) CATALYZED BY ACETOLACTATE DECARBOXYLASE
    DRAKE, AF
    SILIGARDI, G
    CROUT, DHG
    RATHBONE, DL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (24) : 1834 - 1835
  • [4] CHIRAL ALCOHOL-INDUCED DIASTEREOSELECTIVE CONJUGATE ADDITION AND CYCLIZATION
    FANG, CL
    SUEMUNE, H
    SAKAI, K
    [J]. TETRAHEDRON LETTERS, 1990, 31 (33) : 4751 - 4754
  • [5] GANET JP, 1986, TETRAHEDRON LETT, V27, P4573
  • [6] HIGH-YIELD PRODUCTION OF OPTICALLY-ACTIVE 1,2-DIOLS FROM THE CORRESPONDING RACEMATES BY MICROBIAL STEREOINVERSION
    HASEGAWA, J
    OGURA, M
    TSUDA, S
    MAEMOTO, S
    KUTSUKI, H
    OHASHI, T
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (07): : 1819 - 1827
  • [7] CHIRAL CROWN ETHERS DERIVED FROM (+)-(1S, 2S)-TRANS-CYCLOHEXANE-1,2-DIOL
    HAYWARD, RC
    OVERTON, CH
    WHITHAM, GH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (22): : 2413 - 2415
  • [8] APPLICATION OF CHIRAL CYCLIC DIOLS TO ASYMMETRIC ALKYLATION
    KATO, K
    SUEMUNE, H
    SAKAI, K
    [J]. TETRAHEDRON LETTERS, 1992, 33 (02) : 247 - 250
  • [9] C2 SYMMETRY AND ASYMMETRIC INDUCTION
    WHITESELL, JK
    [J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1581 - 1590
  • [10] ZIFFER H, 1975, TETRAHEDRON LETT, P2137