Enantioselective Biocatalytic Reduction of Non-protected Hydroxyacetophenones

被引:5
作者
Neupert, Adrian [1 ]
Ress, Tina [1 ]
Wittmann, Juergen [1 ]
Hummel, Werner [2 ]
Groeger, Harald [1 ]
机构
[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany
[2] Univ Dusseldorf, Forschungszentrum Julich, Inst Mol Enzyme Technol, D-52426 Julich, Germany
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2010年 / 65卷 / 03期
关键词
Alcohols; Asymmetric Synthesis; Biocatalysis; Enzymes; Reduction; ALCOHOL-DEHYDROGENASE; ASYMMETRIC REDUCTION; (S)-ALCOHOL DEHYDROGENASE; 2-STEP SYNTHESIS; COMBINATION; SUBSTRATE; EXPRESSION; KETONES; ACCESS;
D O I
10.1515/znb-2010-0317
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Direct enantioselective reduction of 2'-, 3'- and 4'-hydroxyacetophenone without protection of the hydroxy moiety was carried out in the presence of (R)- and (S)-alcohol dehydrogenases as biocatalysts. Whereas reduction of 2'-hydroxyacetophenone gave only low to medium conversions, reduction of 3'- and 4'-hydroxyacetophenone proceeded efficiently leading to the resulting 1-(3-hydroxyphenyl)ethan-1 -ol and 1-(4-hydroxyphenypethan- 1-01 with high conversion (up to > 95%) and excellent enantioselectivity (up to > 99% cc).
引用
收藏
页码:337 / 340
页数:4
相关论文
共 25 条
  • [1] Anastas PT, 1998, GREEN CHEMISTRY, P1
  • [2] Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis
    Baer, Katrin
    Krausser, Marina
    Burda, Edyta
    Hummel, Werner
    Berkessel, Albrecht
    Groeger, Harald
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) : 9355 - 9358
  • [3] Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with "Designer Cells"
    Berkessel, Albrecht
    Rollmann, Claudia
    Chamouleau, Francoise
    Labs, Stefanie
    May, Oliver
    Groger, Harald
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2697 - 2704
  • [4] BUCHHOLZ S, 2006, BIOCATALYSIS PHARM B, P757
  • [5] Burda E., 2008, Angew. Chem, V120, P9693, DOI DOI 10.1002/ANIE.200801341
  • [6] Modular Chemoenzymatic One-Pot Syntheses in Aqueous Media: Combination of a Palladium-Catalyzed Cross-Coupling with an Asymmetric Biotransformation
    Burda, Edyta
    Hummel, Werner
    Groeger, Harald
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (49) : 9551 - 9554
  • [7] A FACILE GENERAL-ROUTE TO ENANTIOMERIC 1-(4-HYDROXYPHENYL)ALKANOLS, AND AN IMPROVED SYNTHESIS OF 4-VINYLPHENOL
    EVERHART, ET
    CRAIG, JC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07): : 1701 - 1707
  • [8] Enantioselective reduction of 4-fluoroacetophenone at high substrate concentration using a tailor-made recombinant whole-cell catalyst
    Groeger, Harald
    Rollmann, Claudia
    Chamouleau, Francoise
    Sebastien, Isabelle
    May, Oliver
    Wienand, Wolfgang
    Drauz, Karlheinz
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) : 709 - 712
  • [9] Preparative asymmetric reduction of ketones in a biphasic medium with an (S)-alcohol dehydrogenase under in situ-cofactor-recycling with a formate dehydrogenase
    Gröger, H
    Hummel, W
    Rollmann, C
    Chamouleau, F
    Hüsken, H
    Werner, H
    Wunderlich, C
    Abokitse, K
    Drauz, K
    Buchholz, S
    [J]. TETRAHEDRON, 2004, 60 (03) : 633 - 640
  • [10] Practical asymmetric enzymatic reduction through discovery of a dehydrogenase-compatible biphasic reaction media
    Gröger, H
    Hummel, W
    Buchholz, S
    Drauz, K
    Nguyen, TV
    Rollmann, C
    Hüsken, H
    Abokitse, K
    [J]. ORGANIC LETTERS, 2003, 5 (02) : 173 - 176