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  Whole-Cell-Catalyzed Multiple Regio- and Stereoselective Functionalizations in Cascade Reactions Enabled by Directed Evolution

Li, A., Ilie, A., Sun, Z., Lonsdale, R., Xu, J.-H., & Reetz, M. T. (2016). Whole-Cell-Catalyzed Multiple Regio- and Stereoselective Functionalizations in Cascade Reactions Enabled by Directed Evolution. Angewandte Chemie International Edition, 55(39), 12026-12029. doi:10.1002/anie.201605990.

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 Creators:
Li, Aitao1, Author
Ilie, Adriana1, Author              
Sun, Zhoutong1, Author              
Lonsdale, Richard1, Author              
Xu, Jian-He 2, Author
Reetz, Manfred T.3, Author              
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China, ou_persistent22              
3Philipps-Universität Marburg, Fachbereich Chemie, ou_persistent22              

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Free keywords: cascade reactions · C-H activation · directed evolution · enantioselectivity · P450 monooxygenase
 Abstract: Biocatalytic cascade reactions using isolated stereoselective enzymes or whole cells in one-pot processes lead to value-added chiral products in a single workup. The concept has been restricted mainly to starting materials and intermediate products that are accepted by the respective wild-type enzymes. In the present study, we exploited directed evolution as a means to create E. coli whole cells for regio- and stereoselective cascade sequences that are not possible using man-made catalysts. The approach is illustrated using P450-BM3 in combination with appropriate alcohol dehydrogenases as catalysts in either two-, three-, or four-step cascade reactions starting from cyclohexane, cyclohexanol, or cyclohexanone, respectively, leading to either (R,R)-, (S,S)-, or meso-cyclohexane-1,2-diol. The one-pot conversion of cyclohexane into (R)- or (S)-2-hydroxycyclohexanone in the absence of ADH is also described.

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Language(s): eng - English
 Dates: 2016-08-302016-09-19
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201605990
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 55 (39) Sequence Number: - Start / End Page: 12026 - 12029 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851