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  Biotransformations of gamma-methyl-beta-ketosulfones: Stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts

Svatoš, A., Hunkova, Z., Kren, V., Hoskovec, M., Saman, D., Valterova, I., et al. (1996). Biotransformations of gamma-methyl-beta-ketosulfones: Stereoselectivity of 3-methyl-1-(phenylsulfonyl)hexan-2-one reductions by various yeasts. Tetrahedron: Asymmetry, 7(5), 1285-1294. doi:10.1016/0957-4166(96)00145-0.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0015-0F31-3 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0015-0F32-1
Genre: Journal Article

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 Creators:
Svatoš, Aleš1, Author           
Hunkova, Z, Author
Kren, V, Author
Hoskovec, M, Author
Saman, D, Author
Valterova, I, Author
Vrkoc, J, Author
Koutek, B, Author
Affiliations:
1External Organizations, ou_persistent22              

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Free keywords: PHEROMONE SYNTHESIS; CIGARETTE BEETLE; KETO-SULFONES; SEX-PHEROMONE; ACID; STEREOCHEMISTRY
 Abstract: The stereoselectivity of the reduction of rac-3-methyl1-(phenylsulfonyl)hexan-2-one (1) to 3-methyl1-(phenylsulfonyl)hexan-2-ol (2) diastereomers by more than 20 yeasts was studied. Reduction of carbonyl group in 1 proceeds with a high Re-face enantioselectivity: Candida guillermondii (98.9% e.e.), C. zeylanoides (>99.9%), and Kloeckera apiculata (99.6%), respectively and the (R)-1 enantiomer usually reacted faster. The enantioselectivity was determined by GC on chiral cyclodextrine phases and absolute configurations of products were assigned by NMR spectroscopy and a chemical correlation. Copyright (C) 1996 Elsevier Science Ltd

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 Dates: 1996-05
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: ISI: A1996UL78900016
DOI: 10.1016/0957-4166(96)00145-0
Other: EXT286
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Title: Tetrahedron: Asymmetry
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 7 (5) Sequence Number: - Start / End Page: 1285 - 1294 Identifier: ISSN: 0957-4166
CoNE: https://pure.mpg.de/cone/journals/resource/954925577039