Biocatalytic Michael-type additions of acetaldehyde to nitroolefins with the proline-based enzyme 4-oxalocrotonate tautomerase yielding enantioenriched γ-nitroaldehydes.

Authors :: Geertsema EM
Miao Y
Tepper PG
de Haan P
Zandvoort E
Poelarends GJ
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2013 Oct 18; Vol. 19 (43), pp. 14407-10. Date of Electronic Publication: 2013 Sep 24.
Publication Year :: 2013
Abstract: Call me Michaelase: The enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes the Michael-type addition of acetaldehyde to a collection of aromatic and aliphatic nitroolefins with high stereoselectivity producing precursors of γ-aminobutyric acid (GABA) analogues.<br /> (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Acetaldehyde chemistry
Alkenes chemistry
Biocatalysis
Carbon chemistry
Stereoisomerism
gamma-Aminobutyric Acid metabolism
Acetaldehyde metabolism
Alkenes metabolism
Isomerases metabolism
Nitro Compounds chemistry
Proline chemistry

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