Deracemisation of racemic compounds is still the most important strategy to produce optically pure compounds despite many recent advances in asymmetric synthesis. Especially deracemisation approaches that give rise to single enantiomers are preferred, which can be achieved either by invoking organocatalysts, metal complexes or enzymes - leading to dynamic kinetic resolution - or by applying other deracemisation techniques based on stereoinversion or enantioconvergence. In this tutorial review, we will provide an overview of new, recently developed approaches that lead to the important goal of creating organic compounds of single chirality.
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Deracemisation and stereoinversion by a nanoconfined bidirectional enzyme cascade: dual control by electrochemistry and selective metal ion activation.
Chem Commun (Camb)
October 2022
Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK.
The unique ability of the 'electrochemical leaf' (e-Leaf) to drive and control nanoconfined enzyme cascades bidirectionally, while directly monitoring their rate in real-time as electrical current, is exploited to achieve deracemisation and stereoinversion of secondary alcohols using a single electrode in one pot. Two alcohol dehydrogenase enzymes with opposing enantioselectivities, from (selective for ) and (selective for ) are driven bidirectionally coupling to the fast and quasi-reversible interconversion of NADP/NADPH catalysed by ferredoxin NADP reductase - all enzymes being co-entrapped in a nanoporous indium tin oxide electrode. Activity of the enzyme depends on the binding of a non-catalytic Mg, allowing it to be switched off after an oxidative half-cycle, by adding EDTA - the -selective enzyme, with a tightly-bound Zn, remaining fully active.
View Article and Find Full Text PDFMapping the substrate scope of monoamine oxidase (MAO-N) as a synthetic tool for the enantioselective synthesis of chiral amines.
Bioorg Med Chem
April 2018
School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN Manchester, United Kingdom. Electronic address:
A library of 132 racemic chiral amines (α-substituted methylbenzylamines, benzhydrylamines, 1,2,3,4-tetrahydronaphthylamines (THNs), indanylamines, allylic and homoallylic amines, propargyl amines) was screened against the most versatile monoamine oxidase (MAO-N) variants D5, D9 and D11. MAO-N D9 exhibited the highest activity for most substrates and was applied to the deracemisation of a comprehensive set of selected primary amines. In all cases, excellent enantioselectivity was achieved (e.
View Article and Find Full Text PDFBiocatalytic deracemisation of aliphatic β-hydroxy esters: improving the enantioselectivity by optimisation of reaction parameters.
J Ind Microbiol Biotechnol
February 2015
Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, 600 036, India.
Optically pure aliphatic β-hydroxy esters were prepared from their racemates by deracemisation using the biocatalyst Candida parapsilosis ATCC 7330. High optical purity (up to >99 %) and good yields (up to 71 %) of the product secondary alcohols were obtained. This study highlights the importance of optimization of reaction conditions using ethyl-3-hydroxybutanoate as the model substrate to improve the enantioselectivity (enantiomeric excess from 9 to 98 %).
View Article and Find Full Text PDFRecent advances in enzymatic and chemical deracemisation of racemic compounds.
Chem Soc Rev
December 2013
Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
Deracemisation of racemic compounds is still the most important strategy to produce optically pure compounds despite many recent advances in asymmetric synthesis. Especially deracemisation approaches that give rise to single enantiomers are preferred, which can be achieved either by invoking organocatalysts, metal complexes or enzymes - leading to dynamic kinetic resolution - or by applying other deracemisation techniques based on stereoinversion or enantioconvergence. In this tutorial review, we will provide an overview of new, recently developed approaches that lead to the important goal of creating organic compounds of single chirality.
View Article and Find Full Text PDFScreening of microorganisms producing cold-active oxidoreductases to be applied in enantioselective alcohol oxidation. An Antarctic survey.
Mar Drugs
November 2011
Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes 748, SP 05508-900, São Paulo, Brazil.
Several microorganisms were isolated from soil/sediment samples of Antarctic Peninsula. The enrichment technique using (RS)-1-(phenyl)ethanol as a carbon source allowed us to isolate 232 psychrophile/psychrotroph microorganisms. We also evaluated the enzyme activity (oxidoreductases) for enantioselective oxidation reactions, by using derivatives of (RS)-1-(phenyl)ethanol as substrates.
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