Bridging between organocatalysis and biocatalysis: asymmetric addition of acetaldehyde to β-nitrostyrenes catalyzed by a promiscuous proline-based tautomerase | Health & Environmental Research Online (HERO)

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HERO ID

1062163

Reference Type

Journal Article

Title

Bridging between organocatalysis and biocatalysis: asymmetric addition of acetaldehyde to β-nitrostyrenes catalyzed by a promiscuous proline-based tautomerase

Author(s)

Zandvoort, E; Geertsema, EM; Baas, BJ; Quax, WJ; Poelarends, GJ

Year

2012

Is Peer Reviewed?

Yes

Journal

Angewandte Chemie (International Edition)
ISSN: 1433-7851
EISSN: 1521-3773

Volume

Issue

Page Numbers

1240-1243

Language

English

PMID

22190406

DOI

10.1002/anie.201107404

Web of Science Id

WOS:000305180400047

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84856182835&doi=10.1002%2fanie.201107404&partnerID=40&md5=5e6798b0f731ef4d87f891d4ca9151a7
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Abstract

Non-natural beauty: The enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously (i.e., with non-natural activity) catalyzes the Michael-type addition of acetaldehyde to nitrostyrene. Catalysis likely proceeds via enamine formation of the amino-terminal proline residue of 4-OT with acetaldehyde (see picture), reminiscent of organocatalysis. High stereoselectivity, low catalyst loading, and water as reaction medium characterize this methodology. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

Chemistry