Enantioselective hydrolyses with Yarrowia lipolytica:: a versatile strain for esters, enol esters, epoxides, and lactones

被引:19
作者
Fantin, G [1 ]
Fogagnolo, M [1 ]
Guerrini, A [1 ]
Medici, A [1 ]
Pedrini, P [1 ]
Fontana, S [1 ]
机构
[1] Univ Ferrara, Dipartmento Chim, I-44100 Ferrara, Italy
关键词
D O I
10.1016/S0957-4166(01)00463-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Racemic secondary esters 1-3, gamma -lactones 8 9, and styrene oxide 7 are kinetically resolved via hydrolysis with Yarrowia lipolytica YL2 strain. The enantioselective hydrolysis of prochiral enol esters 4 6 to the corresponding homochiral carbonyl compounds 13-15 is also described. Subsequent reduction of the ketone 13 and of the aldehyde 15 can be avoided using lyophilised cells. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2709 / 2713
页数:5
相关论文
共 31 条
  • [11] THE STEREOCONTROLLED FORMATION OF 1,2,3-TRIOLS BY YEAST-MEDIATED TRANSFORMATION OF ALPHA-KETO EPOXIDES
    FOUCHE, G
    HORAK, RM
    METHCOHN, O
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) : 119 - 120
  • [13] GALL M, 1988, ORG SYNTH, V50-9, P121
  • [14] Stereospecific enzymatic hydrolysis of racemic epoxide: a process for making chiral epoxide
    Goswami, A
    Totleben, MJ
    Singh, AK
    Patel, RN
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (16) : 3167 - 3175
  • [15] ENANTIOSELECTIVE HYDROLYSIS OF 2-METHYLCYCLOHEXANYL ACETATES WITH THE CULTURED-CELLS OF MARCHANTIA-POLYMORPHA
    HIRATA, T
    IZUMI, S
    AKITA, K
    YOSHIDA, H
    GOTOH, S
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1465 - 1466
  • [16] BIOCATALYTIC PREPARATION OF BICYCLO[3.2.0]HEPTANE DERIVATIVES
    KLEMPIER, N
    GEYMAYER, P
    STADLER, P
    FABER, K
    GRIENGL, H
    [J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (02) : 111 - 118
  • [17] Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides:: stereoselectivity and use for kinetic resolution and asymmetrization
    Matoishi, K
    Sano, A
    Imai, N
    Yamazaki, T
    Yokoyama, M
    Sugai, T
    Ohta, H
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (07) : 1097 - 1102
  • [18] ENZYME-MEDIATED ENANTIOFACE-DIFFERENTIATING HYDROLYSIS OF ALPHA-SUBSTITUTED CYCLOALKANONE ENOL ESTERS
    MATSUMOTO, K
    TSUTSUMI, S
    IHORI, T
    OHTA, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) : 9614 - 9619
  • [19] Matsumoto K, 1998, CHEM LETT, P283
  • [20] An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ270
    MethCohn, O
    Wang, MX
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (08): : 1099 - 1104