Asymmetric reduction of acetophenone in membrane reactors: comparison of oxazaborolidine and alcohol dehydrogenase catalysed processes

被引:51
作者
Rissom, S [1 ]
Beliczey, J [1 ]
Giffels, G [1 ]
Kragl, U [1 ]
Wandrey, C [1 ]
机构
[1] Forschungszentrum Julich, Inst Biotechnol, D-52425 Julich, Germany
关键词
D O I
10.1016/S0957-4166(99)00050-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enantioselective reduction of acetophenone was studied in two different ways. Chemical borane reduction using a homogeneously soluble polymer-bound oxazaborolidine catalyst was carried out in a continuously operated membrane reactor and yielded (R)-phenylethanol in good enantiomeric excess with high space-time yields. An enzymatic reduction using a dehydrogenase two-enzyme system as the catalyst and formate as the hydrogen source was carried out in an extractive bi-membrane reactor and yielded (S)-phenylethanol in excellent enantiomeric excess with a low enzyme consumption. A comparison of the two systems with respect to space-time yield, total turnover number and other parameters is made. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:923 / 928
页数:6
相关论文
共 25 条
  • [11] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH CHIRAL ALKOXY-AMINE-BORANE COMPLEXES
    HIRAO, A
    ITSUNO, S
    NAKAHAMA, S
    YAMAZAKI, N
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) : 315 - 317
  • [12] HUMMEL W, 1990, APPL MICROBIOL BIOT, V34, P15, DOI 10.1007/BF00170916
  • [13] ENZYME-CATALYZED SYNTHESIS OF OPTICALLY PURE R(+)-PHENYLETHANOL
    HUMMEL, W
    [J]. BIOTECHNOLOGY LETTERS, 1990, 12 (06) : 403 - 408
  • [14] DEHYDROGENASES FOR THE SYNTHESIS OF CHIRAL COMPOUNDS
    HUMMEL, W
    KULA, MR
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1989, 184 (01): : 1 - 13
  • [15] ASYMMETRIC REDUCTION OF ALIPHATIC-KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE
    ITSUNO, S
    ITO, K
    HIRAO, A
    NAKAHAMA, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) : 555 - 557
  • [16] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE
    ITSUNO, S
    ITO, K
    HIRAO, A
    NAKAHAMA, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (08) : 469 - 470
  • [17] Kruse W, 1996, RECL TRAV CHIM PAY B, V115, P239
  • [18] A novel reactor concept for the enzymatic reduction of poorly soluble ketones
    Liese, A
    Zelinski, T
    Kula, MR
    Kierkels, H
    Karutz, M
    Kragl, U
    Wandrey, C
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 4 (1-2) : 91 - 99
  • [19] Noyori R., 1994, ASYMMETRIC CATALYSIS
  • [20] A NOVEL NADH-DEPENDENT CARBONYL REDUCTASE WITH AN EXTREMELY BROAD SUBSTRATE RANGE FROM CANDIDA-PARAPSILOSIS - PURIFICATION AND CHARACTERIZATION
    PETERS, J
    MINUTH, T
    KULA, MR
    [J]. ENZYME AND MICROBIAL TECHNOLOGY, 1993, 15 (11) : 950 - 958