Directed evolution of cyclohexanone monooxygenases: Enantioselective biocatalysts for the oxidation of prochiral thioethers

被引:88
作者
Reetz, MT [1 ]
Daligault, F [1 ]
Brunner, B [1 ]
Hinrichs, H [1 ]
Deege, A [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
asymmetric catalysis; directed evolution; enzyme catalysis; protein engineering; sulfoxides;
D O I
10.1002/anie.200460311
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mutational changes in cyclohexanone monooxygenases (CHMOs), for example the introduction of serine at position 432, lead to surprisingly versatile enantioselective biocatalysts that perform particularly well in the air-mediated partial oxidation of prochiral thioethers (see scheme).
引用
收藏
页码:4078 / 4081
页数:4
相关论文
共 43 条
  • [1] A highly enantioselective biocatalytic sulfoxidation by the topsoil bacterium Pseudomonas frederiksbergensis
    Adam, W
    Heckel, F
    Saha-Möller, CR
    Taupp, M
    Schreier, P
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (06) : 983 - 985
  • [2] Microbiological transformations .36. Preparative scale synthesis of chiral thioacetal and thioketal sulfoxides using whole-cell biotransformations
    Alphand, V
    Gaggero, N
    Colonna, S
    Pasta, P
    Furstoss, R
    [J]. TETRAHEDRON, 1997, 53 (28) : 9695 - 9706
  • [3] Microbiological transformations .35. Enantioselective one-step preparative scale synthesis of 1,3-dithiane-1-oxide via whole-cell bacterial oxidation.
    Alphand, V
    Gaggero, N
    Colonna, S
    Furstoss, R
    [J]. TETRAHEDRON LETTERS, 1996, 37 (34) : 6117 - 6120
  • [4] [Anonymous], 1997, ANGEW CHEM
  • [5] [Anonymous], CATALYTIC ASYMMETRIC
  • [6] SPECIES-STRAIN DEPENDENCE OF STEREOSELECTIVITY IN MICROBIAL OXIDATION OF THIOETHERS
    AURET, BJ
    BOYD, DR
    HENBEST, HB
    WATSON, CG
    BALENOVI.K
    POLAK, V
    JOHANIDE.V
    DIVJAK, S
    [J]. PHYTOCHEMISTRY, 1974, 13 (01) : 65 - 68
  • [7] STEREOSELECTIVE ENZYME-CATALYZED OXIDATION-REDUCTION REACTIONS OF THIOACETALS-THIOACETAL SULFOXIDES BY FUNGI
    AURET, BJ
    BOYD, DR
    BREEN, F
    GREENE, RME
    ROBINSON, PM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03): : 930 - 933
  • [8] Cadwell R C, 1992, PCR Methods Appl, V2, P28, DOI 10.1101/gr.2.1.28
  • [9] EFFECTS OF SUBSTRATE STRUCTURE ON THE ENANTIOSELECTIVITY AND STEREOCHEMICAL COURSE OF SULFOXIDATION CATALYZED BY CYCLOHEXANONE MONOOXYGENASE
    CARREA, G
    REDIGOLO, B
    RIVA, S
    COLONNA, S
    GAGGERO, N
    BATTISTEL, E
    BIANCHI, D
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (08) : 1063 - 1068
  • [10] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299