Biocatalytic reductive aminations with NAD(P)H-dependent enzymes: enzyme discovery, engineering and synthetic applications

Chemical Society Reviews, Год журнала: 2023, Номер 53(1), С. 227 - 262

Опубликована: Дек. 7, 2023

This review summarized NAD(P)H-dependent amine dehydrogenases and imine reductases which catalyzes asymmetric reductive amination to produce optically active amines.

Язык: Английский

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Multifunctional Biocatalysts for Organic Synthesis

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(12), С. 7876 - 7884

Опубликована: Март 15, 2024

Biocatalysis is becoming an indispensable tool in organic synthesis due to high enzymatic catalytic efficiency as well exquisite chemo- and stereoselectivity. Some biocatalysts display great promiscuity including a broad substrate scope the ability catalyze more than one type of transformation. These promiscuous activities have been applied individually efficiently access numerous valuable target molecules. However, systems which enzymes possessing multiple different are less developed. Such multifunctional (MFBs) would simplify chemical by reducing number operational steps enzyme count, simplifying sequence space that needs be engineered develop efficient biocatalyst. In this Perspective, we highlight recently reported MFBs focusing on their synthetic utility mechanism. We also offer insight into origin comment potential strategies for discovery engineering.

Язык: Английский

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Imine Reductases and Reductive Aminases in Organic Synthesis

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 14308 - 14329

Опубликована: Сен. 12, 2024

Язык: Английский

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Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(26), С. 14221 - 14226

Опубликована: Июнь 22, 2023

Piperidines are frequently found in natural products and of importance to the pharmaceutical industry. A generally useful asymmetric route enantiomerically enriched 3-substituted piperidines remains elusive. Here we report a cross-coupling approach enantioenriched 3-piperidines from pyridine- sp2-hybridized boronic acids. The key step involves Rh-catalyzed reductive Heck reaction aryl, heteroaryl, or vinyl acids phenyl pyridine-1(2H)-carboxylate provide tetrahydropyridines high yield excellent enantioselectivity with wide functional group tolerance. three-step process involving i) partial reduction pyridine, ii) carbometalation, then iii) another provides access variety 3-piperidines, including clinically used materials such as Preclamol Niraparib.

Язык: Английский

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Chemo-enzymatic synthesis of chiral 3-substituted tetrahydroquinolines by a sequential biocatalytic cascade and Buchwald–Hartwig cyclization

Green Chemistry, Год журнала: 2023, Номер 25(12), С. 4667 - 4673

Опубликована: Янв. 1, 2023

A one-pot bienzymatic cascade was developed to synthesize ( S )- N -(3-aryl-2-methylpropyl) prop-2-en-1-amines from α,β-unsaturated aldehydes, and 3-substituted tetrahydroquinolines were prepared via Buchwald–Hartwig amination deallylation.

Язык: Английский

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The Impact of Metagenomics on Biocatalysis

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(21)

Опубликована: Март 18, 2024

Abstract In the ever‐growing demand for sustainable ways to produce high‐value small molecules, biocatalysis has come forefront of greener routes these chemicals. As such, need constantly find and optimise suitable biocatalysts specific transformations never been greater. Metagenome mining shown rapidly expand toolkit promiscuous enzymes needed new transformations, without requiring protein engineering steps. If is needed, metagenomic candidate can often provide a better starting point than previously discovered enzyme on open database or from literature, instance. this review, we highlight where metagenomics made substantial impact area in recent years. We review discovery unexplored ‘hidden’ sequence space, leading characterisation with enhanced properties that originate natural selection pressures native environments.

Язык: Английский

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Synthesis of Dihydropyridine Spirocycles by Semi-Pinacol-Driven Dearomatization of Pyridines

Organic Letters, Год журнала: 2023, Номер 25(2), С. 400 - 404

Опубликована: Янв. 10, 2023

The identification of the beneficial pharmacokinetic properties aza-spirocycles has led to routine incorporation these highly rigid and three-dimensional structures in pharmaceuticals. Herein, we report an operationally simple synthesis spirocyclic dihydropyridines via electrophile-induced dearomative semi-pinacol rearrangement 4-(1'-hydroxycyclobutyl)pyridines. various points for diversification spirocyclization precursors, as well synthetic utility amine ketone functionalities products, provide potential rapidly assemble medicinally relevant spirocycles.

Язык: Английский

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Bifunctional Imine Reductase Cascades for the Synthesis of Saturated N-Heterocycles

ACS Catalysis, Год журнала: 2024, Номер 14(19), С. 14703 - 14710

Опубликована: Сен. 19, 2024

Saturated

Язык: Английский

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Modular Construction of Chiral Aminopiperidine via Palladium-Catalyzed Hydroamination of 1,2-Dihydropyridine

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 12, 2025

In this study, we describe a generally straightforward methodology for the catalytic synthesis of chiral aminopiperidine from pyridine and azoles. The key step was palladium-catalyzed regioselective N–H insertion into double bond 1,2-dihydropyridine. This hydroamination exhibits wide substrate scope functional group compatibility. Mechanistic study revealed that C═C followed cis addition. utility protocol demonstrated by diverse functionalization enamine bond.

Язык: Английский

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Chemoenzymatic two-step synthesis of tartaric acid employing glucose oxidase in combination with bimetallic AuPt/TiO2 catalyst

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Март 1, 2025

Язык: Английский

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