Literature DB >> 17165947

Asymmetric bioreductions of beta-nitro acrylates as a route to chiral beta2-amino acids.

Magdalena A Swiderska1, Jon D Stewart.   

Abstract

[Structure: see text] Reductions of beta-nitroacrylates by Saccharomyces carlsbergensis old yellow enzyme is the key step in a concise route to optically active beta2-amino acids. The enzymatic reductions occur with 87-96% ee, with larger substrates providing greater stereoselectivities. This work extends enantioselective enzymatic alkene reductions to include acyclic systems with weakly coordinating substituents.

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Year:  2006        PMID: 17165947     DOI: 10.1021/ol062612f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Structure-Based Insight into the Asymmetric Bioreduction of the C=C Double Bond of alpha,beta-Unsaturated Nitroalkenes by Pentaerythritol Tetranitrate Reductase.

Authors:  Helen S Toogood; Anna Fryszkowska; Victoria Hare; Karl Fisher; Anna Roujeinikova; David Leys; John M Gardiner; Gill M Stephens; Nigel S Scrutton
Journal:  Adv Synth Catal       Date:  2008-11-17       Impact factor: 5.837

2.  Asymmetric Reduction of Activated Alkenes by Pentaerythritol Tetranitrate Reductase: Specificity and Control of Stereochemical Outcome by Reaction Optimisation.

Authors:  Anna Fryszkowska; Helen Toogood; Michiyo Sakuma; John M Gardiner; Gill M Stephens; Nigel S Scrutton
Journal:  Adv Synth Catal       Date:  2009-11       Impact factor: 5.837

Review 3.  Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds.

Authors:  Christoph K Winkler; Gábor Tasnádi; Dorina Clay; Mélanie Hall; Kurt Faber
Journal:  J Biotechnol       Date:  2012-04-04       Impact factor: 3.307

4.  Asymmetric bioreduction of activated carbon-carbon double bonds using Shewanella yellow enzyme (SYE-4) as novel enoate reductase.

Authors:  Naseem Iqbal; Florian Rudroff; Ann Brigé; Jozef Van Beeumen; Marko D Mihovilovic
Journal:  Tetrahedron       Date:  2012-09-16       Impact factor: 2.457

5.  Chemoenzymatic asymmetric synthesis of pregabalin precursors via asymmetric bioreduction of β-cyanoacrylate esters using ene-reductases.

Authors:  Christoph K Winkler; Dorina Clay; Simon Davies; Pat O'Neill; Paul McDaid; Sebastien Debarge; Jeremy Steflik; Mike Karmilowicz; John W Wong; Kurt Faber
Journal:  J Org Chem       Date:  2013-01-28       Impact factor: 4.354

6.  Catalytic Performance of a Class III Old Yellow Enzyme and Its Cysteine Variants.

Authors:  Anika Scholtissek; Eric Gädke; Caroline E Paul; Adrie H Westphal; Willem J H van Berkel; Dirk Tischler
Journal:  Front Microbiol       Date:  2018-10-12       Impact factor: 5.640

7.  Metals in Biotechnology: Cr-Driven Stereoselective Reduction of Conjugated C=C Double Bonds.

Authors:  Marine C R Rauch; Yann Gallou; Léna Delorme; Caroline E Paul; Isabel W C E Arends; Frank Hollmann
Journal:  Chembiochem       Date:  2019-12-19       Impact factor: 3.164

Review 8.  "A Study in Yellow": Investigations in the Stereoselectivity of Ene-Reductases.

Authors:  Fabio Parmeggiani; Elisabetta Brenna; Danilo Colombo; Francesco G Gatti; Francesca Tentori; Davide Tessaro
Journal:  Chembiochem       Date:  2021-10-13       Impact factor: 3.461

  8 in total

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