Microbial reduction of alpha-substituted-alpha-acetyl-gamma-butyrolactones

被引:9
作者
Ribeiro, Joyce B. [1 ]
Sousa, L. M. A. [1 ]
Fraga, C. A. M. [1 ,2 ]
Leite, Selma G. F. [3 ]
Ramos, M. C. K. V. [1 ]
de Aquino Neto, F. R. [1 ]
Aguiar, L. C. S. [4 ]
de Souza, Rodrigo O. M. A. [1 ,4 ]
Antunes, O. A. C. [1 ,4 ]
机构
[1] Univ Fed Rio de Janeiro, Inst Quim, BR-21941909 Rio de Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Fac Farm, BR-21941614 Rio de Janeiro, Brazil
[3] Univ Fed Rio de Janeiro, Escola Quim, BR-21941909 Rio de Janeiro, Brazil
[4] Univ Fed Rio de Janeiro, NPPN, BR-21941614 Rio de Janeiro, Brazil
关键词
yeasts; mold; reduction; chiral;
D O I
10.1016/j.catcom.2008.02.012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The microbial reduction of alpha-methyl, allyl and benzyl derivatives of alpha-acetyl-gamma-butyrolactones was carried out. It has been shown that different microorganisms, Kluyveromyces marxianus, Hansenula sp., Geotrichum candidum and Aspergillus niger, arc capable to carry out the enantiospecific/selective reduction of these compounds. In the examples studied K marxianus afforded the best results in terms of diastereo and enantioselectivity. It was found that depending on the particular microorganism used, a particular enantiomer can be obtained. Since these microorganisms are wild type, that is, are not engineered, they are robust and can be used to scale up these processes, which is going to be the next step of our study. It has been definitively proved that this microbial reduction occurs via the keto form, so clarifying the mechanism of these reactions firstly carried out with unsubstituted compounds. (c) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:1782 / 1786
页数:5
相关论文
共 19 条
  • [1] BARCO A, 1973, SYNTHESIS-STUTTGART, P316
  • [2] Microbial reduction of ethyl 2-oxo-4-phenylbutyrate.: Searching for R-enantioselectivity.: New access to the enalapril like ACE inhibitors
    Bergo de Lacerda, Paulo S.
    Ribeiro, Joyce Benzaquem
    Leite, Selma G. F.
    Ferrara, Maria Antonieta
    Coelho, Ricardo B.
    Bon, Elba P. S.
    Luiz da Silva Lima, Edson
    Antunes, O. A. C.
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (08) : 1186 - 1188
  • [3] Microbial enantioselective reduction of ethyl-2-oxo-4-phenyl-butanoate
    de Lacerda, PSB
    Ribeiro, JB
    Leite, SGF
    Coelho, RB
    Lima, ELD
    Antunes, OAC
    [J]. BIOCHEMICAL ENGINEERING JOURNAL, 2006, 28 (03) : 299 - 302
  • [4] SYNTHESIS OF HOMOCHIRAL SYN AND ANTI-ALPHA-(HYDROXYETHYL)-GAMMA-BUTYROLACTONES VIA MICROBIAL REDUCTION
    FANTIN, G
    FOGAGNOLO, M
    GIOVANNINI, P
    MEDICI, A
    PAGNOTTA, E
    PEDRINI, P
    TRINCONE, A
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (09) : 1631 - 1634
  • [5] Kinetic aspects involved in the simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
    Gonçalves, LPB
    Antunes, OAC
    Pinto, GF
    Oestreicher, EG
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 124 (02) : 219 - 227
  • [6] Enzymatic laboratory scale production of homochiral (R)-3-fluorolactic acid methyl ester via enantiospecific reduction of sodium fluoropyruvate catalyzed by rabbit muscle L-lactate dehydrogenase (L-LDH)
    Goncalves, LPB
    Antunes, OAC
    Pinto, GF
    Oestreicher, EG
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (05) : 1237 - 1240
  • [7] Kinetic aspects of the enantiospecific reduction of sodium 3-fluoropyruvate catalyzed by rabbit muscle L-lactate dehydrogenase: Production of homochiral (R)-3-fluorolactic acid methyl ester
    Goncalves, LPB
    Antunes, OAC
    Pinto, GF
    Oestreicher, EG
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 4 (1-2) : 67 - 76
  • [8] Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
    Gonçalves, LPB
    Antunes, OAC
    Pinto, GF
    Oestreicher, EG
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (07) : 1465 - 1468
  • [9] Biocatalysis from the perspective of an industrial practitioner: let a biocatalyst do a job that no chemocatalyst can
    Ikunaka, M
    [J]. CATALYSIS TODAY, 2004, 96 (03) : 93 - 102
  • [10] Screening yeasts for the stereoselective reduction of oxoester clofibrate analogues
    Perrone, MG
    Santandrea, E
    Scilimati, A
    Syldatk, C
    Tortorella, V
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (08) : 1473 - 1477