Enantioselective C-C bond synthesis catalysed by enzymes

被引:119
作者
Sukumaran, J [1 ]
Hanefeld, U [1 ]
机构
[1] Tech Univ Delft, NL-2628 BL Delft, Netherlands
关键词
D O I
10.1039/b412490a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of C-C bonds is often the pivotal step of a synthesis. Nature has made a variety of versatile enzymes available that catalyse this type of reaction very selectively under mild conditions. Cyanohydrins, acyloins (alpha-hydroxy ketones), alpha-hydroxy acids and aldols (beta-hydroxy ketones) are very efficiently synthesised enantioselectively with the aid of C-C bond forming enzymes, which we discuss in this tutorial review. In the case of the alpha-hydroxy acids the applications of nitrilases in a synthetic dkr even allows a disconnection that has no enantioselective chemical equivalent.
引用
收藏
页码:530 / 542
页数:13
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共 46 条
  • [1] RETRACTED: The nitrile-degrading enzymes: current status and future prospects (Retracted article. See vol. 100, pg. 7359, 2016)
    Banerjee, A
    Sharma, R
    Banerjee, UC
    [J]. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2002, 60 (1-2) : 33 - 44
  • [2] Industrial methods for the production of optically active intermediates
    Breuer, M
    Ditrich, K
    Habicher, T
    Hauer, B
    Kesseler, M
    Stürmer, R
    Zelinski, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 788 - 824
  • [3] BRUSSEE J, 2000, STEREOSELECTIVE BIOC, P289
  • [4] Bühler H, 2000, CHEM-EUR J, V6, P2564, DOI 10.1002/1521-3765(20000717)6:14<2564::AID-CHEM2564>3.0.CO
  • [5] 2-F
  • [6] Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues
    Crestia, D
    Demuynck, C
    Bolte, J
    [J]. TETRAHEDRON, 2004, 60 (10) : 2417 - 2425
  • [7] Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde
    Demir, AS
    Sesenoglu, Ö
    Dunkelmann, P
    Muller, M
    [J]. ORGANIC LETTERS, 2003, 5 (12) : 2047 - 2050
  • [8] Enzyme catalyzed hydroxymethylation of aromatic aldehydes with formaldehyde.: Synthesis of hydroxyacetophenones and (S)-benzoins
    Demir, AS
    Ayhan, P
    Igdir, AC
    Duygu, AN
    [J]. TETRAHEDRON, 2004, 60 (31) : 6509 - 6512
  • [9] An enzyme library approach to biocatalysis: Development of nitrilases for enantioselective production of carboxylic acid derivatives
    DeSantis, G
    Zhu, ZL
    Greenberg, WA
    Wong, KV
    Chaplin, J
    Hanson, SR
    Farwell, B
    Nicholson, LW
    Rand, CL
    Weiner, DP
    Robertson, DE
    Burk, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) : 9024 - 9025
  • [10] Development of a donor-acceptor concept for enzymatic cross-coupling reactions of aldehydes:: The first asymmetric cross-benzoin condensation
    Dünkelmann, P
    Kolter-Jung, D
    Nitsche, A
    Demir, AS
    Siegert, P
    Lingen, B
    Baumann, M
    Pohl, M
    Müller, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) : 12084 - 12085