| Biocatalytical production of (5S)-hydroxy-2-hexanone. | |
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MedLine Citation:
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PMID: 19109675 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Michael Katzberg; Kerstin Wechler; Marion Müller; Pascal Dünkelmann; Jürgen Stohrer; Werner Hummel; Martin Bertau |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-11-17 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 7 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2009 Jan |
Date Detail:
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Created Date: 2008-12-25 Completed Date: 2009-02-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 304-14 Citation Subset: IM |
Affiliation:
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Institute of Biochemistry, Dresden University of Technology, Dresden, D-01062, Dresden, Germany. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Alcohol Dehydrogenase
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metabolism Biocatalysis Catalysis Hexanones / chemistry*, metabolism Saccharomyces cerevisiae / enzymology, metabolism Thermoanaerobacter / metabolism |
| Chemical | |
Reg. No./Substance:
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0/5-hydroxy-2-hexanone; 0/Hexanones; EC 1.1.1.1/Alcohol Dehydrogenase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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