Update 1 of: Enantioselective Enzymatic Desymmetrizations in Organic Synthesis

被引:132
作者
Garcia-Urdiales, Eduardo [1 ]
Alfonso, Ignacio [2 ]
Gotor, Vicente [1 ]
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, Fac Quim, E-33006 Oviedo, Spain
[2] CSIC, Dept Quim Biol & Modelizac Mol, Inst Quim Avanzada Cataluna IQAC, ES-08034 Barcelona, Spain
关键词
BAEYER-VILLIGER MONOOXYGENASES; RECOMBINANT ESCHERICHIA-COLI; ASYMMETRIC TOTAL-SYNTHESIS; LIPASE-CATALYZED DESYMMETRIZATION; YEAST MEDIATED BIOHYDROGENATION; SECONDARY ALCOHOL-DEHYDROGENASE; PROCHIRAL 2,2-DISUBSTITUTED 1,3-PROPANEDIOLS; EFFICIENT CHEMOENZYMATIC SYNTHESIS; BIOCATALYTIC KETONE REDUCTION; 2-SUBSTITUTED ALLYL ALCOHOLS;
D O I
10.1021/cr100330u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various developments made towards the use of biocatalysts for the desymmetrization of meso and prochiral compounds are reviewed. Studied have found that the hydrolysis of meso epoxides generally displays low enantioselectivities. Fukuyama and co-workers reported the total synthesis of Leustroducsin, a potent colonystimulating factor inducer isolated from the culture broth of Streptomyces platensis SANK 60191. Prati and co-workers have carried out the Amano PS lipasecatalyzed desymmetrization of aziridine, whose monoacetylated derivative, obtained in high yield and ee, is related to a key intermediate used in the total synthesis of the already mentioned antibiotic FR-900482. Sugai and co-workers have investigated the substrate specificity of the reduction of different triketones with the yeast strain Torulaspora delbrueckii IFO10921.
引用
收藏
页码:PR110 / PR180
页数:71
相关论文
共 615 条
  • [1] A rational design of phosphonium salt type ionic liquids for ionic liquid coated-lipase catalyzed reaction
    Abe, Yoshikazu
    Yoshiyama, Kazuhide
    Yagi, Yusuke
    Hayase, Shuichi
    Kawatsura, Motoi
    Itoh, Toshiyuki
    [J]. GREEN CHEMISTRY, 2010, 12 (11) : 1976 - 1980
  • [2] α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidase of peas (Pisum sativum):: A novel biocatalytic synthesis of enantiomerically pure (R)-2-hydroxy acids
    Adam, W
    Boland, W
    Hartmann-Schreier, J
    Humpf, HU
    Lazarus, M
    Saffert, A
    Saha-Moller, CR
    Schreier, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) : 11044 - 11048
  • [3] 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
  • [4] Adam W, 2000, EUR J ORG CHEM, V2000, P2923, DOI 10.1002/1099-0690(200008)2000:16<2923::AID-EJOC2923>3.0.CO
  • [5] 2-L
  • [6] Biocatalytic asymmetric hydroxylation of hydrocarbons by free and immobilized Bacillus megaterium cells
    Adam, W
    Lukacs, Z
    Kahle, C
    Saha-Möller, CR
    Schreier, P
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 11 (4-6) : 377 - 385
  • [7] Biocatalytic asymmetric hydroxylation of hydrocarbons with the topsoil-microorganism Bacillus megaterium
    Adam, W
    Lukacs, Z
    Harmsen, D
    Saha-Möller, CR
    Schreier, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) : 878 - 882
  • [8] Akai S, 2000, CHEM PHARM BULL, V48, P1519
  • [9] Asymmetric total synthesis of fredericamycin A: An intramolecular cycloaddition pathway
    Akai, S
    Tsujino, T
    Fukuda, N
    Iio, K
    Takeda, Y
    Kawaguchi, K
    Naka, T
    Higuchi, K
    Akiyama, E
    Fujioka, H
    Kita, Y
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (21) : 6286 - 6297
  • [10] Enantiodivergent preparation of optically active oxindoles having a stereogenic quaternary carbon center at the C3 position via the lipase-catalyzed desymmetrization protocol: Effective use of 2-furoates for either enzymatic esterification or hydrolysis
    Akai, S
    Tsujino, T
    Akiyama, E
    Tanimoto, K
    Naka, T
    Kita, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2478 - 2486