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Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase

Paper ID Volume ID Publish Year Pages File Format Full-Text
17096 42640 2013 7 PDF Available
Title
Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase
Abstract

Unspecific peroxygenases (EC 1.11.2.1) represent a group of secreted heme-thiolate proteins that are capable of catalyzing the mono-oxygenation of diverse organic compounds, using only H2O2 as a co-substrate. Here we show that the peroxygenase secreted by the fungus Agrocybe aegerita catalyzed the oxidation of 20 different alkenes. Five branched alkenes, among them 2,3-dimethyl-2-butene and cis-2-butene, as well as propene and butadiene were epoxidized with complete regioselectivity. Longer linear alkenes with a terminal double bond (e.g. 1-octene) and cyclic alkenes (e.g. cyclohexene) were converted into the corresponding epoxides and allylic hydroxylation products; oxidation of the cyclic monoterpene limonene yielded three oxygenation products (two epoxides and an alcohol). In the case of 1-alkenes, the conversion occurred with moderate stereoselectivity, in which the preponderance for the (S)-enantiomer reached up to 72% ee for the epoxide product. The apparent Michaelis–Menten constant (Km) for the epoxidation of the model substrate 2-methyl-2-butene was 5 mM, the turnover number (kcat) 1.3 × 103 s−1 and the calculated catalytic efficiency, kcat/Km, was 2.5 × 105 M−1 s−1. As epoxides represent chemical building blocks of high relevance, new enzymatic epoxidation pathways are of interest to complement existing chemical and biotechnological approaches. Stable and versatile peroxygenases as that of A. aegerita may form a promising biocatalytic platform for the development of such enzyme-based syntheses.

► The peroxygenase of A. aegerita catalyzes the epoxidation of diverse alkenes. ► The reactions proceed with high regioselectivity. ► The reactions proceed with stereoselectivity of up to 72% ee.

Keywords
Biocatalysis; Heme-thiolate; Oxygenation; Peroxygenase; Stereoselective
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Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 52, Issues 6–7, 10 May 2013, Pages 370–376
Authors
, , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us