Literature DB >> 24115023

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

Edzard M Geertsema1, Yufeng Miao, Pieter G Tepper, Pim de Haan, Ellen Zandvoort, Gerrit J Poelarends.   

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.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C-C bond formation; Michael-type addition; aminobutyric acid; biocatalysis; enzymes

Mesh：

Substances：

Year:  2013        PMID： 24115023     DOI： 10.1002/chem.201302351

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  16 in total

1.  Stereochemical Control of Enzymatic Carbon-Carbon Bond-Forming Michael-Type Additions by "Substrate Engineering".

Authors:  Yufeng Miao; Pieter G Tepper; Edzard M Geertsema; Gerrit J Poelarends
Journal:  European J Org Chem       Date:  2016-10-25

2.  Engineering a Promiscuous Tautomerase into a More Efficient Aldolase for Self-Condensations of Linear Aliphatic Aldehydes.

Authors:  Mehran Rahimi; Jan-Ytzen van der Meer; Edzard M Geertsema; Gerrit J Poelarends
Journal:  Chembiochem       Date:  2017-05-30       Impact factor: 3.164

3.  Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase.

Authors:  Guangcai Xu; Michele Crotti; Thangavelu Saravanan; Kim M Kataja; Gerrit J Poelarends
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-14       Impact factor: 15.336

4.  Substituting the catalytic proline of 4-oxalocrotonate tautomerase with non-canonical analogues reveals a finely tuned catalytic system.

Authors:  Michael S Lukesch; Tea Pavkov-Keller; Karl Gruber; Klaus Zangger; Birgit Wiltschi
Journal:  Sci Rep       Date:  2019-02-25       Impact factor: 4.379

5.  Enantioselective Synthesis of Pharmaceutically Active γ-Aminobutyric Acids Using a Tailor-Made Artificial Michaelase in One-Pot Cascade Reactions.

Authors:  Lieuwe Biewenga; Thangavelu Saravanan; Andreas Kunzendorf; Jan-Ytzen van der Meer; Tjaard Pijning; Pieter G Tepper; Ronald van Merkerk; Simon J Charnock; Andy-Mark W H Thunnissen; Gerrit J Poelarends
Journal:  ACS Catal       Date:  2019-01-07       Impact factor: 13.084

6.  Demethionylation of Pro-1 variants of 4-oxalocrotonate tautomerase in Escherichia coli by co-expression with an engineered methionine aminopeptidase.

Authors:  Bert-Jan Baas; Ellen Zandvoort; Anna A Wasiel; Gerrit J Poelarends
Journal:  FEBS Open Bio       Date:  2014-07-09       Impact factor: 2.693

7.  Using mutability landscapes of a promiscuous tautomerase to guide the engineering of enantioselective Michaelases.

Authors:  Jan-Ytzen van der Meer; Harshwardhan Poddar; Bert-Jan Baas; Yufeng Miao; Mehran Rahimi; Andreas Kunzendorf; Ronald van Merkerk; Pieter G Tepper; Edzard M Geertsema; Andy-Mark W H Thunnissen; Wim J Quax; Gerrit J Poelarends
Journal:  Nat Commun       Date:  2016-03-08       Impact factor: 14.919

Review 8.  The Generation and Exploitation of Protein Mutability Landscapes for Enzyme Engineering.

Authors:  Jan-Ytzen van der Meer; Lieuwe Biewenga; Gerrit J Poelarends
Journal:  Chembiochem       Date:  2016-08-19       Impact factor: 3.164

9.  In Situ Acetaldehyde Synthesis for Carboligation Reactions.

Authors:  Lieuwe Biewenga; Andreas Kunzendorf; Gerrit J Poelarends
Journal:  Chembiochem       Date:  2020-02-12       Impact factor: 3.164

10.  Tuning Enzyme Activity for Nonaqueous Solvents: Engineering an Enantioselective "Michaelase" for Catalysis in High Concentrations of Ethanol.

Authors:  Chao Guo; Lieuwe Biewenga; Max Lubberink; Ronald van Merkerk; Gerrit J Poelarends
Journal:  Chembiochem       Date:  2020-02-18       Impact factor: 3.164
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