| Epoxide-hydrolase-initiated hydrolysis/rearrangement cascade of a methylene-interrupted bis-epoxide yields chiral THF moieties without involvement of a "cyclase". | |
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MedLine Citation:
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PMID: 19496106 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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In contrast with electrophilic enzyme-catalysed cyclisations in terpenoid biosynthesis, cyclisations of tetrahydrofuran moieties found in several groups of natural products, such as annonaceous acetogenins, neurofurans and phytooxylipins, appear to proceed through a nucleophilic cascade mechanism starting from bis-epoxy fatty acid precursors. This hypothesis was verified by epoxide-hydrolase-catalysed hydrolytic ring-opening/cyclisation cascades starting from a methylene-interrupted meso-bis-epoxide model substrate, which furnished the corresponding THF products with excellent de and ee values. Molecular modelling showed that the points of enzyme attack were consistent with the stereospecificities of the enzymes, whereas the stereochemical courses of the cyclisation were solely governed by Baldwin's rules and did not invoke the involvements of a "cyclase". |
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Authors:
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Barbara T Ueberbacher; Gustav Oberdorfer; Karl Gruber; Kurt Faber |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chembiochem : a European journal of chemical biology Volume: 10 ISSN: 1439-7633 ISO Abbreviation: Chembiochem Publication Date: 2009 Jul |
Date Detail:
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Created Date: 2009-07-14 Completed Date: 2009-10-08 Revised Date: 2011-04-06 |
Medline Journal Info:
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Nlm Unique ID: 100937360 Medline TA: Chembiochem Country: Germany |
Other Details:
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Languages: eng Pagination: 1697-704 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, Graz, Austria. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Biocatalysis Biotransformation Catalytic Domain Computer Simulation Cyclization Epoxide Hydrolases / chemistry, metabolism* Epoxy Compounds / chemistry*, metabolism Furans / chemistry*, metabolism Hydrolysis Protein Structure, Tertiary Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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W 901-B12//Austrian Science Fund FWF |
| Chemical | |
Reg. No./Substance:
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0/Epoxy Compounds; 0/Furans; 109-99-9/tetrahydrofuran; EC 3.3.2.-/Epoxide Hydrolases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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