Literature DB >> 16478171

A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines.

Colin J Dunsmore1, Reuben Carr, Toni Fleming, Nicholas J Turner.   

Abstract

Deracemization of racemic chiral tertiary amines has been achieved by combination of an enantioselective amine oxidase, obtained through directed evolution, and ammonia borane in a one-pot process.

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Year:  2006        PMID: 16478171     DOI: 10.1021/ja058536d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

1.  Nicotinic pharmacophore: the pyridine N of nicotine and carbonyl of acetylcholine hydrogen bond across a subunit interface to a backbone NH.

Authors:  Angela P Blum; Henry A Lester; Dennis A Dougherty
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-28       Impact factor: 11.205

2.  Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Authors:  Aaron D Lackner; Andrew V Samant; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

3.  Cloning, expression, purification, crystallization and preliminary X-ray diffraction analysis of variants of monoamine oxidase from Aspergillus niger.

Authors:  Kate E Atkin; Renate Reiss; Nicholas J Turner; Andrzej M Brzozowski; Gideon Grogan
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2008-02-23

Review 4.  Directed evolution drives the next generation of biocatalysts.

Authors:  Nicholas J Turner
Journal:  Nat Chem Biol       Date:  2009-08       Impact factor: 15.040

5.  Synthetic utility of one-pot chemoenzymatic reaction sequences.

Authors:  Tyler J Doyon; Alison R H Narayan
Journal:  Synlett       Date:  2019-06-06       Impact factor: 2.454

6.  Combining a Clostridial enzyme exhibiting unusual active site plasticity with a remarkably facile sigmatropic rearrangement: rapid, stereocontrolled entry into densely functionalized fluorinated phosphonates for chemical biology.

Authors:  Kaushik Panigrahi; Gregory A Applegate; Guillaume Malik; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2015-03-05       Impact factor: 15.419

7.  Development of dynamic kinetic resolution on large scale for (±)-1-phenylethylamine.

Authors:  Lisa K Thalén; Jan-E Bäckvall
Journal:  Beilstein J Org Chem       Date:  2010-09-13       Impact factor: 2.883

8.  Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: ethanol as tunable nicotinamide reductant.

Authors:  Sylvain Broussy; Ross W Cheloha; David B Berkowitz
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

9.  Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540.

Authors:  Erik W van Hellemond; Marianne van Dijk; Dominic P H M Heuts; Dick B Janssen; Marco W Fraaije
Journal:  Appl Microbiol Biotechnol       Date:  2008-01-09       Impact factor: 4.813

10.  Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters.

Authors:  Satish S More; T Krishna Mohan; Y Sateesh Kumar; U K Syam Kumar; Navin B Patel
Journal:  Beilstein J Org Chem       Date:  2011-06-20       Impact factor: 2.883

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