Document Detail

Biocatalytical production of (5S)-hydroxy-2-hexanone.
MedLine Citation:
PMID:  19109675     Owner:  NLM     Status:  MEDLINE    
Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, which is produced with high enantioselectivity (ee >99%). Since (S)-2 can be reduced further to furnish (2S,5S)-hexanediol ((2S,5S)-3), chemoselectivity is a major issue. Among the tested biocatalysts the whole-cell system S. cerevisiae L13 surpasses the bacterial dehydrogenase ADH-T in terms of chemoselectivity. The use of whole-cells of S. cerevisiae L13 affords (S)-2 from prochiral 1 with 85% yield, which is 21% more than the value obtained with ADH-T. This is due to the different reaction rates of monoreduction (1-->2) and consecutive reduction (2-->3) of the respective biocatalysts. In order to optimise the performance of the whole-cell-bioreduction 1 2 with S. cerevisiae, the system was studied in detail, revealing interactions between cell-physiology and xenobiotic substrate and by-products, respectively. This study compares the whole-cell biocatalytic route with the enzymatic route to enantiopure (S)-2 and investigates factors determining performance and outcome of the bioreductions.
Michael Katzberg; Kerstin Wechler; Marion Müller; Pascal Dünkelmann; Jürgen Stohrer; Werner Hummel; Martin Bertau
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-11-17
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  7     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2008-12-25     Completed Date:  2009-02-13     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  304-14     Citation Subset:  IM    
Institute of Biochemistry, Dresden University of Technology, Dresden, D-01062, Dresden, Germany.
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MeSH Terms
Alcohol Dehydrogenase / metabolism
Hexanones / chemistry*,  metabolism
Saccharomyces cerevisiae / enzymology,  metabolism
Thermoanaerobacter / metabolism
Reg. No./Substance:
0/5-hydroxy-2-hexanone; 0/Hexanones; EC Dehydrogenase

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