| Asymmetric direduction of 1,2-indanedione to cis (1S,2R) indanediol by Trichosporon cutaneum MY 1506. | |
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MedLine Citation:
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PMID: 16232651 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Cis (1S,2R) indanediol is a potential precursor to (-)-cis (1S,2R)-1-aminoindan-2-ol, a key chiral synthon for a leading HIV protease inhibitor, Crixivan (Indinavir). A potential route to the biosynthesis of this important precursor, the microbial asymmetric direduction of 1,2-indanedione to its corresponding diol, cis (1S,2R) indanediol, was investigated. The screening of 32 yeast strains yielded Trichosporon cutaneum MY 1506 as a suitable biocatalyst. At the 2-l shake-flask scale, 1,2-indanedione (charged at 1.0 g/l) was bioconverted to cis (1S,2R) indanediol at a final bioconversion yield of 99.1% and an enantiomeric excess of >99%. When scaled up in a 23-l bioreactor, T. cutaneum produced 8.4 g of pure cis (1S,2R) indanediol, and the isolated yield of cis (1S,2R) indanediol was 52%. Purification of the scale-up also yielded 0.9 g of the more polar trans (1S,2R) indanediol diastereomer, a minor bioreduction product. Supercritical fluid chromatography analyses of the purified cis (1S,2R) and trans (1S,2S) indanediol demonstrated that the enantiomeric excesses during this bioconversion scale-up were 99% and 26%, respectively. |
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Authors:
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S Stahl; N Ikemoto; A King; R Greasham; M Chartrain |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of bioscience and bioengineering Volume: 88 ISSN: 1389-1723 ISO Abbreviation: J. Biosci. Bioeng. Publication Date: 1999 |
Date Detail:
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Created Date: 2005-10-19 Completed Date: 2005-11-01 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100888800 Medline TA: J Biosci Bioeng Country: Japan |
Other Details:
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Languages: eng Pagination: 495-9 Citation Subset: - |
Affiliation:
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Department of Bioprocess R&D, Merck Research Laboratories, RY80Y-105, Rahway, NJ 07065, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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