Chapter 9. Synthesis of Chiral sec-Alcohols by Ketone Reduction

  1. John Whittall6 and
  2. Peter Sutton7
  1. David Pollard1,
  2. Matthew Truppo1,
  3. Jeffrey Moore1,
  4. Birgit Kosjek1,
  5. David Tellers1,
  6. Jeffrey Moore1,
  7. Ioulia Smonou2,
  8. Dimitris Kalaitzakis2,
  9. Musa M. Musa3,
  10. Karla I. Ziegelmann-Fjeld4,
  11. Claire Vieille4,
  12. J. Gregory Zeikus4,
  13. Robert S. Phillipsa3,
  14. Matthew Truppo1,
  15. Krista Morley1,
  16. David Pollard1,
  17. Paul Devine1,
  18. Tadashi Ema5,
  19. Nobuyasu Okita5,
  20. Sayaka Ide5 and
  21. Takashi Sakai5

Published Online: 15 DEC 2009

DOI: 10.1002/9780470748589.ch9

Practical Methods for Biocatalysis and Biotransformations

Practical Methods for Biocatalysis and Biotransformations

How to Cite

Pollard, D., Truppo, M., Moore, J., Kosjek, B., Tellers, D., Moore, J., Smonou, I., Kalaitzakis, D., Musa, M. M., Ziegelmann-Fjeld, K. I., Vieille, C., Zeikus, J. G., Phillipsa, R. S., Truppo, M., Morley, K., Pollard, D., Devine, P., Ema, T., Okita, N., Ide, S. and Sakai, T. (2009) Synthesis of Chiral sec-Alcohols by Ketone Reduction, in Practical Methods for Biocatalysis and Biotransformations (eds J. Whittall and P. Sutton), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9780470748589.ch9

Editor Information

  1. 6

    Manchester Interdisciplinary Biocentre, University of Manchester, United Kingdom

  2. 7

    GlaxoSmithKline, Synthetic Chemistry, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK

Author Information

  1. 1

    Process Research, Merck Research Laboratories, Merck & Co. Inc., Rahway, NJ, USA

  2. 2

    Department of Chemistry, University of Crete, Iraklion-Voutes, 71003 Crete, Greece

  3. 3

    Department of Chemistry and of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602, USA

  4. 4

    Biochemistry and Molecular Biology, Michigan State University, East Lansing, MI 48824, USA

  5. 5

    Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama 700-8530, Japan

Publication History

  1. Published Online: 15 DEC 2009
  2. Published Print: 18 DEC 2009

ISBN Information

Print ISBN: 9780470519271

Online ISBN: 9780470748589

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Keywords:

  • synthesis of chiral sec-alcohols by ketone reduction;
  • alcohol dehydrogenase ADH-RE;
  • asymmetric synthesis of (S)-Bis(trifluoromethyl)phenylethanol;
  • enantioselective and diastereoselective enzyme-catalyzed dynamic kinetic resolution of unsaturated ketone;
  • ketoreductase reduction of ketone 1;
  • nicotinamide adenine dinucleotidephosphate(NADPH)-dependent ketoreductases(KREDs);
  • enzyme-catalysed stereoselective reduction of diketones/keto esters to keto alcohols/hydroxy esters;
  • thermoanaerobacter ethanolicus (W110A TeSADH);
  • ketoreductase reduction of diaryl ketones;
  • screening of ketoreductase enzymes

Summary

This chapter contains sections titled:

  • Asymmetric Synthesis of (S)-Bis(trifluoromethyl)phenylethanol by Biocatalytic Reduction of Bis(trifluoromethyl)acetophenone

  • Enantioselective and Diastereoselective Enzyme-catalyzed Dynamic Kinetic Resolution of an Unsaturated Ketone

  • Enzyme-catalysed Synthesis of α-Alkyl-β-hydroxy Ketones and Esters by Isolated Ketoreductases

  • Asymmetric Reduction of Phenyl Ring-containing Ketones Using Xerogel-encapsulated W110A Secondary Alcohol Dehydrogenase from Thermoanaerobacter ethanolicus

  • (R)- and (S)-Enantioselective Diaryl Methanol Synthesis Using Enzymatic Reduction of Diaryl Ketones

  • Highly Enantioselective and Efficient Synthesis of Methyl (R)-o-Chloromandelate, Key Intermediate for Clopidogrel Synthesis, with Recombinant Escherichia coli