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New Stetter reactions catalyzed by thiamine diphosphate dependent MenD from E. coli

Paper ID Volume ID Publish Year Pages File Format Full-Text
22999 43409 2014 5 PDF Available
Title
New Stetter reactions catalyzed by thiamine diphosphate dependent MenD from E. coli
Abstract

•Acrylate, methacrylate and derivatives as substrates for enzymatic CC bond formation.•Unexpected substrate and reaction range of thiamine-dependent MenD.•Enzymatic Stetter reactions as a more general feature of thiamine-dependent enzymes.

The intermolecular asymmetric Stetter reaction is a rarely found biocatalysts transformation. MenD, the second enzyme of the menaquinone biosynthetic pathway, catalyzes as a physiological reaction a Stetter-like addition of α-ketoglutarate to isochorismate. The substrate range of MenD for similar 1,4-additions is highly restricted. All other thiamine diphosphate dependent enzymes known to act as stetterases are members of the PigD enzyme subfamily, which accept aliphatic and aromatic α,β-unsaturated ketones and thioesters as Michael acceptor substrates. Here, we describe the unexpected activity of MenD with short-chain α,β-unsaturated acids and derivatives as substrates in Stetter reactions. MenD possesses a characteristic substrate range with respect to Michael acceptor substrates which is distinctly different from the classical stetterases. This provides biocatalytic access to new types of products which are not related to the products currently accessible by thiamine diphosphate dependent enzyme catalysis.

Keywords
23-CHD, (5S,6S)-5,6-dihydroxycyclohexa-1,3-diencarboxylic acid; Kgd, alpha-ketoglutarate decarboxylase; MenD, 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase; PigD, sequence-homologous enzymes from Saccharapolyspora erythraea; SHCH
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New Stetter reactions catalyzed by thiamine diphosphate dependent MenD from E. coli
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 191, 10 December 2014, Pages 64–68
Authors
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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