Journal
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Volume 61, Issue 3-4, Pages 284-288Publisher
ELSEVIER
DOI: 10.1016/j.molcatb.2009.08.007
Keywords
Enantioselective; Substituted fluorenone; Plant biocatalysts; Surfactant; Anti-Prelog's rule
Funding
- Fok Ying Tung Education Foundation
- National Natural Science Foundation of China [20536010, 20576016, 20676021]
- State Key Laboratory of Bioreactor Engineering at East China University of Science and Technology
- Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
- Ministry of Education Key Laboratory of Pesticide & Chemical Biology at Central China Normal University
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Various fruits and vegetables have been evaluated as biocatalysts in the enantioselective reduction of substituted fluorenones under mild and eco-friendly conditions. Grape exhibited the best results with 99% ee and 97% conversion. The conversion rate varies in the presence of different surfactants, but the enantioselectivity remains unchanged. That is, enantiomeric selectivity is from biocatalysts anti the conversion is related to the aqueous solubility of substrates. The surfactant. Triton X-100, is the best for improving the biotransformation anti behaved in a concentration-dependent manner. The high enantioselectivity of halogen substituents is attributed to halogen electron-withdrawing effects rather than electron-donating effects like -CH3, but the yield is not dependent on the size of the halogens. It is interesting that the absolute configuration of the product, 2-chloro-fluorenol, is R not S, indicating its biocatalytic reduction following anti-Prelog's rule. This study provided a useful method for the reduction of rigid macro-cyclic aromatic ketones. (C) 2009 Elsevier B.V. All rights reserved.
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