Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 369301
Title Stereoselectivity and substrate specificity in the kinetic resolution of methyl-substituted 1-oxaspiro[2.5]octanes by Rhodotorula glutinis epoxide hydrolase
Author(s) Weijers, C.A.G.M.; Meeuwse, P.; Herpers, R.L.J.M.; Franssen, M.C.R.; Sudhölter, E.J.R.
Source Journal of Organic Chemistry 70 (2005)17. - ISSN 0022-3263 - p. 6639 - 6646.
DOI https://doi.org/10.1021/jo050533w
Department(s) Laboratory for Organic Chemistry
Bioprocess Engineering
Wageningen UR Administration OfficeCorporate Staff
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2005
Keyword(s) ylide-mediated epoxidation - methionine aminopeptidase - spectrophotometric assay - angiogenesis inhibitors - efficient synthesis - fumagillin analogs - terminal epoxides - hydrolysis - ketones - stereochemistry
Abstract [GRAPHICS] The kinetic resolution of a range of methyl-substituted 1-oxaspiro[2.5]octanes by yeast epoxide hydrolase (YEH) from Rhodotorula glutinis has been investigated. The structural determinants of substrate specificity and stereoselectivity of YEH toward these substrates appeared to be the configuration of the epoxide ring and the substitution pattern of the cyclohexane ring. For all compounds tested, O-axial epoxides were hydrolyzed faster than the corresponding O-equatorial compounds. In concern of the ring substituents,.YEH preferred methyl groups on the Re side of the ring. Placement of substituents close to the spiroepoxide carbon decreased the reaction rate but increased enantioselectivity. YEH-catalyzed kinetic resolutions of 4-methyl 1-oxaspiro [2.5] octane epimers were most enantioselective,(E > 100).
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