Development of an <i>R</i>‐Selective Amine Oxidase with Broad Substrate Specificity and High Enantioselectivity

Heath, Rachel S.; Pontini, Marta; Bechi, Beatrice; Turner, Nicholas J.

doi:10.1002/cctc.201301008

Cited by 70 publications

(58 citation statements)

References 39 publications

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“…In recent years, the preparation of chiral non‐carboxyl substituted THIQs have been intensively investigated using redox biocatalysis . Most notably are the applications of recombinant amine oxidase variants developed by Turner and coworkers, which have been used in the chemo‐enzymatic synthesis of chiral 1‐alkyl‐, benzyl‐ or aryl‐substituted THIQs (Scheme A) –. These enzymatic routes are cost‐effective and generally produce excellent enantioselectivity and yield.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Approach to (S)‐1,2,3,4‐Tetrahydroisoquinoline Carboxylic Acids Employing D‐Amino Acid Oxidase

Qian

et al. 2019

Adv Synth Catal

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Optically pure 1,2,3,4‐tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4‐tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D‐amino acid oxidase from Fusarium solani M‐0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1‐ and 3‐carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)‐enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia‐borane in one pot, deracemization of these racemic carboxyl‐substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative‐scale deracemization of racemic 1,2,3,4‐tetrahydroisoquinoline‐1‐carboxylic acid and 1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylic acid was also demonstrated with good isolated yields (82% and 73%, respectively) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4‐tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl‐substituted 1,2,3,4‐tetrahydroquinolines and 1,2,3,4‐tetrahydro‐ß‐carbolines.

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Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Approach to (S)‐1,2,3,4‐Tetrahydroisoquinoline Carboxylic Acids Employing D‐Amino Acid Oxidase

Qian

et al. 2019

Adv Synth Catal

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“…In a different approach, the combination of engineered amine oxidases (AOs) and imine reductases (IREDs) in a one‐pot reaction, allowed for deracemisation by the stereoinversion of cyclic amines, affording enantioenriched 2‐substituted pyrrolidines ( 4 ) with high yields and ee values (Scheme ). In this approach, starting from the racemic amine, either the ( S )‐selective monoamine oxidase from Aspergillus niger (MAO‐N) or the ( R )‐selective 6‐hydroxy‐ d ‐nicotine oxidase (E350L/E352D variant) from Arthrobacter nicotinovorans (6‐HDNO), selectively oxidise one enantiomer of amine 4 to the imine 5 , whereas the antipode remains intact. Then, the IRED stereoselectively reduces the formed imine into the amine but of opposite handedness.…”

Section: Enzymatic Deracemisation Proceduresmentioning

confidence: 99%

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

et al. 2020

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Deracemisation methods have demonstrated their importance in the preparation of chiral compounds in the last few years. In order to resolve a racemic mixture in a dynamic sense, one enantiomer of the starting material can be converted to the other through a deracemisation procedure, that can be achieved by different mechanisms based on stereoinversion or enantioconvergence, often involving two‐opposite half reactions, with at least one of the reactions being enantioselective enough to finally obtain an enantioenriched chiral compound. The focus of this comprehensive review is on the application of deracemisation procedures in the present century in order to obtain optically active valuable compounds when employing non‐metallic catalysts. Thus, the review will mainly focus on the use of different enzymatic preparations (purified enzymes, cell‐free extracts or whole cell systems) and organocatalysts for the deracemisation of racemic mixtures.

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“…Accordingly, a one-pot/two-step methodology allowed the direct conversion of diallyl malonates into cyclic monoacid esters in aqueous media (Scheme 13C). Recently, and following this idea (Ru-catalyzed RCM + enzymatic organic transformations), Turner, Castagnolo and co-workers have reported the combination of the Ru-catalyzed ring-closing metathesis of diallyl anilines (to produce the corresponding 3-pyrrolines) and the subsequent biocatalytic aromatization of the resulting heterocycles (mediated by whole cells containing monoamine oxidases MAO-N variants D5, D9 and D11 [82][83][84] or the nicotine oxidase biocatalyst 6-HDNO (HDNO = 6-hydroxy-D-nicotine oxidase) [85]) for the synthesis of pyrroles in aqueous media (Scheme 14) [77]. In this case, and in contrast to the aforementioned results reported by Gröger, the authors firstly parametrized the biocatalytic transformation, thus studying the aromatization of different 3-pyrrolines promoted by monoamine oxidases MAO-N or 6-HDNO (Scheme 14A).…”

Section: Combination Of Ru-catalyzed Ring-closing Metathesis Of Diallmentioning

confidence: 99%

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

2018

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During the last decade, the combination of different metal-and bio-catalyzed organic reactions in aqueous media has permitted the flourishing of a variety of one-pot asymmetric multi-catalytic reactions devoted to the construction of enantiopure and high added-value chemicals under mild reaction conditions (usually room temperature) and in the presence of air. Herein, a comprehensive account of the state-of-the-art in the development of catalytic networks by combining metallic and biological catalysts in aqueous media (the natural environment of enzymes) is presented. Among others, the combination of metal-catalyzed isomerizations, cycloadditions, hydrations, olefin metathesis, oxidations, C-C cross-coupling and hydrogenation reactions, with several biocatalyzed transformations of organic groups (enzymatic reduction, epoxidation, halogenation or ester hydrolysis), are discussed.

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Development of an R‐Selective Amine Oxidase with Broad Substrate Specificity and High Enantioselectivity

Cited by 70 publications

References 39 publications

Chemoenzymatic Approach to (S)‐1,2,3,4‐Tetrahydroisoquinoline Carboxylic Acids Employing D‐Amino Acid Oxidase

Chemoenzymatic Approach to (S)‐1,2,3,4‐Tetrahydroisoquinoline Carboxylic Acids Employing D‐Amino Acid Oxidase

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

One-Pot Combination of Metal- and Bio-Catalysis in Water for the Synthesis of Chiral Molecules

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