Journal ArticleDOI
Biocatalytic Imine Reduction and Reductive Amination of Ketones
TLDR
This review provides a comprehensive overview of biocatalytic imine reduction and reductive amination of ketones, highlighting the natural roles, substrate scopes, structural features, and potential application fields of the involved enzymes.Abstract:
Chiral amines represent a prominent functional group in pharmaceuticals and agrochemicals and are hence attractive targets for asymmetric synthesis. Since the pharmaceutical industry has identified biocatalysis as a valuable tool for synthesising chiral molecules with high enantiomeric excess and under mild reaction conditions, enzymatic methods for chiral amine synthesis are increasing in importance. Among the strategies available in this context, the asymmetric reduction of imines by NAD(P)H-dependent enzymes and the related reductive amination of ketones have long remained underrepresented. However, recent years have witnessed an impressive progress in the application of natural or engineered imine-reducing enzymes, such as imine reductases, opine dehydrogenases, amine dehydrogenases, and artificial metalloenzymes. This review provides a comprehensive overview of biocatalytic imine reduction and reductive amination of ketones, highlighting the natural roles, substrate scopes, structural features, and potential application fields of the involved enzymes.read more
Citations
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Journal ArticleDOI
Artificial Biocatalytic Linear Cascades for Preparation of Organic Molecules
TL;DR: The review introduces a systematic classification of the cascades according to the number of enzymes in the linear sequence and differentiates between cascades involving exclusively enzymes and combinations of enzymes with non-natural catalysts or chemical steps.
Journal ArticleDOI
Biocatalysis in the Pharmaceutical Industry: The Need for Speed
TL;DR: Dramatic increases in the speed of protein engineering are needed to deliver on the ever increasing opportunities for industrial biocatalytic processes.
Journal ArticleDOI
A reductive aminase from Aspergillus oryzae
Godwin A. Aleku,Henry Man,Juan Mangas-Sanchez,Sarah L. Montgomery,Mahima Sharma,Friedemann Leipold,Shahed Hussain,Gideon Grogan,Nicholas J. Turner +8 more
TL;DR: Kinetic studies revealed that the enzyme catalysed both the imine formation step, as well as the reduction step, in an NADP(H)-dependent reductive aminase from Aspergillus oryzae that can catalyse the reductive coupling of a broad set of carbonyl compounds with a variety of primary and secondary amines.
Journal ArticleDOI
Enzymatic asymmetric synthesis of chiral amino acids.
TL;DR: This review provides an overview of the reported methods for enzymatic asymmetric synthesis of chiral amino acids, including asymmetric reductive amination of keto acids, asymmetric transfer of an amino group to keto fatty acids, enantioselective addition of ammonia to α,β-unsaturated acids, and aldol condensation ofan amino acid to aldehydes.
Journal ArticleDOI
Enantioselective Chemo- and Biocatalysis: Partners in Retrosynthesis.
TL;DR: The review provides a guide to the use of biocatalytic methods in the area of chemical synthesis with focused attention on retrosynthetic considerations and analysis and is expected to lead to better understanding of the characteristics and distinctions of the two complementary approaches.
References
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Journal ArticleDOI
Engineering the third wave of biocatalysis
Uwe T. Bornscheuer,Gjalt W. Huisman,Romas J. Kazlauskas,Romas J. Kazlauskas,Stefan Lutz,Jeffrey C. Moore,Karen Robins +6 more
TL;DR: Applications of protein-engineered biocatalysts ranging from commodity chemicals to advanced pharmaceutical intermediates that use enzyme catalysis as a key step are discussed.
Journal ArticleDOI
Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture
Christopher Savile,Jacob M. Janey,Emily Mundorff,Jeffrey C. Moore,Sarena Tam,William R. Jarvis,Jeffrey Colbeck,Anke Krebber,Fred J. Fleitz,Jos Brands,Paul N. Devine,Gjalt W. Huisman,Gregory Hughes +12 more
TL;DR: An efficient biocatalytic process to replace a recently implemented rhodium-catalyzed asymmetric enamine hydrogenation for the large-scale manufacture of the antidiabetic compound sitagliptin is reported, underscoring the maturation of bioc atalysis to enable efficient, economical, and environmentally benign processes for the manufacture of pharmaceuticals.
Journal ArticleDOI
Chemistry and biology of siderophores.
Robert C. Hider,Xiaole Kong +1 more
TL;DR: The classification and chemical properties of siderophores are described, before outlining research on sidersophore biosynthesis and transport and Clinically important siderophile design and the therapeutic potential are described.
Journal ArticleDOI
Industrial Methods for the Production of Optically Active Intermediates
Michael Breuer,Klaus Ditrich,Tilo Habicher,Bernhard Hauer,Maria Kesseler,Rainer Stürmer,Thomas Zelinski +6 more
TL;DR: For the industrial implementation of many transformations alternative methods are available and the advantages of the individual methods will be discussed herein and exemplified by syntheses of relevant compounds.
Journal ArticleDOI
Stable incorporation of plasmid DNA into higher plant cells: the molecular basis of crown gall tumorigenesis
Mary-Dell Chilton,Martin H. Drummond,Donald J. Merlo,Daniela Sciaky,Alice L. Montoya,Milton P. Gordon,Eugene W. Nester +6 more
TL;DR: It is presented that crown gall tumors are caused by the incorporation of part of a virulence plasmid carried by the inciting bacterium, Agrobacterium tumefaciens, and the relationship between this plant tumor and virally induced animal tumor systems is discussed.