Recent Progress in the Synthesis of α‐Hydroxy Carbonyl Compounds with ThDP‐dependent Carboligases

ChemCatChem, Год журнала: 2024, Номер 16(15)

Опубликована: Март 18, 2024

Abstract Thiamine diphosphate (ThDP) dependent carboligases catalyze the formation of carbon‐carbon bonds. These enzymes are prominent biocatalysts for production valuable α‐hydroxy carbonyl compounds, which serve as key building blocks in synthesis various pharmaceuticals and fine chemicals. Carboligases act selective manner to afford regio‐ stereochemically defined products from simple starting materials. This review explores catalytic prowess synthetic purposes is aimed at providing a selection tool particular sets substrates or desired products. The comprehensive overview encompasses structural insights, relationships currently known sequence space practical applications with focus on recent literature, showcasing potent tools sustainable efficient synthesis.

Язык: Английский

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Concatenating Microbial, Enzymatic, and Organometallic Catalysis for Integrated Conversion of Renewable Carbon Sources

JACS Au, Год журнала: 2024, Номер 4(12), С. 4546 - 4570

Опубликована: Окт. 21, 2024

The chemical industry can now seize the opportunity to improve sustainability of its processes by replacing fossil carbon sources with renewable alternatives such as CO

Язык: Английский

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Biotransformation of 2-keto-4-hydroxybutyrate via aldol condensation using an efficient and thermostable carboligase from Deinococcus radiodurans

Bioresources and Bioprocessing, Год журнала: 2024, Номер 11(1)

Опубликована: Янв. 16, 2024

Abstract The bioconversion of 4-hydroxy-2-keto acid derivatives via aldol condensation formaldehyde and pyruvate has received substantial attention as potential source chemicals for production amino acids, hydroxy carboxylic chiral aldehydes. We developed an environmentally friendly biocatalyst consisting a novel thermostable class II aldolase from Deinococcus radiodurans with maltose-binding protein (MBP-DrADL), which specific activity 46.3 µmol min –1 mg . Surprisingly, MBP-DrADL maintained over 60% enzyme 4 days at 50 to 65 °C, we used the best candidate produce 2-keto-4-hydroxybutyrate (2-KHB) condensation. optimum reaction conditions 2-KHB were pH 8.0, 5 mM Mg 2+ , 100 formaldehyde, 200 pyruvate. Under these optimized conditions, produced 76.5 (8.94 g L ) 60 volumetric productivity 8.94 h 357.6 mg-enzyme Furthermore, was improved by continuous addition substrates, approximately 124.8 (14.6 14.6 583.4 respectively. showed highest yet reported. Our study provides highly efficient synthesis lays foundation large-scale application high-value compounds formaldehyde. Graphical

Язык: Английский

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Efficient production of 1,2,4-butanetriol from corn cob hydrolysate by metabolically engineered Escherichia coli

Microbial Cell Factories, Год журнала: 2024, Номер 23(1)

Опубликована: Фев. 12, 2024

Abstract Corn cob is a major waste mass-produced in corn agriculture. hydrolysate containing xylose, arabinose, and glucose the hydrolysis product of cob. Herein, recombinant Escherichia coli strain BT-10 was constructed to transform into 1,2,4-butanetriol, platform substance with diversified applications. To eliminate catabolite repression enhance NADPH supply for alcohol dehydrogenase YqhD catalyzed 1,2,4-butanetriol generation, ptsG encoding transporter EIICB Glc pgi phosphoglucose isomerase were deleted. With four heterologous enzymes including xylose dehydrogenase, xylonolactonase, xylonate dehydratase, α-ketoacid decarboxylase endogenous YqhD, E. can produce 36.63 g/L productivity 1.14 g/[L·h] using as substrate. When used substrate, 43.4 generated 1.09 yield 0.9 mol/mol. its desirable characteristics, promising commercial production.

Язык: Английский

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Recent advances in enzymatic carbon–carbon bond formation

RSC Advances, Год журнала: 2024, Номер 14(36), С. 25932 - 25974

Опубликована: Янв. 1, 2024

Enzymatic carbon-carbon (C-C) bond formation reactions have become an effective and invaluable tool for designing new biological medicinal molecules, often with asymmetric features. This review provides a systematic overview of key C-C enzymes, the focus reaction mechanisms recent advances. These include aldol reaction, Henry Knoevenagel condensation, Michael addition, Friedel-Crafts alkylation acylation, Mannich Morita-Baylis-Hillman (MBH) Diels-Alder acyloin condensations

Язык: Английский

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Innovative coupling pathway for second- and third-generation biomass: Efficient L-lactate synthesis from xylose and C1 compounds

Chemical Engineering Journal, Год журнала: 2025, Номер unknown, С. 159573 - 159573

Опубликована: Янв. 1, 2025

Язык: Английский

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Rare Ketose Synthesis from Glycolaldehyde by C2 Elongation of Aldoses Catalyzed by Transketolase Variants

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7979 - 7992

Опубликована: Апрель 29, 2025

Язык: Английский

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Progress in research on the biosynthesis of 1,2,4-butanetriol by engineered microbes

World Journal of Microbiology and Biotechnology, Год журнала: 2024, Номер 40(2)

Опубликована: Янв. 11, 2024

Язык: Английский

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Manipulating Activity and Chemoselectivity of a Benzaldehyde Lyase for Efficient Synthesis of α-Hydroxymethyl Ketones and One-Pot Enantio-Complementary Conversion to 1,2-Diols

ACS Catalysis, Год журнала: 2024, Номер 14(13), С. 9687 - 9700

Опубликована: Июнь 13, 2024

The α-hydroxymethyl ketone motif has been widely found in many pharmaceutically important molecules and used as a key intermediate the synthesis of various fine chemicals natural products. Hydroxymethylation aldehydes with formaldehyde catalyzed by thiamine diphosphate (ThDP)-dependent enzymes is considered highly valuable approach terms atom economics sustainability, while low activity chemoselectivity restricted its widespread application. In this study, benzaldehyde lyase (BAL) high catalytic efficiency was acquired enzyme screening engineering, which hydroxymethylation furfural at concentration 700 mM. Crystal structural analysis molecular dynamics studies revealed that BAL were improved reshaping conformation substrate entrance tunnel. Furthermore, one-pot concurrent enzymatic process involving BAL-catalyzed subsequent asymmetric reduction carbonyl reductase developed, offering efficient way to produce chiral 1,2-diols from simple aldehydes, ee values (97–99%) good yields (52–97%). significantly demonstrated potential engineered industrial production ketones, could readily enable other high-value-added formaldehyde.

Язык: Английский

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A Chemo-Enzymatic Approach for Preparing Efinaconazole with High Optical Yield

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14803 - 14808

Опубликована: Окт. 4, 2023

Herein, we present a novel and ecofriendly biocatalytic approach for synthesizing efinaconazole (7), clinically used antifungal agent. This method involves utilizing benzaldehyde lyase (BAL) to catalyze the crucial benzoin condensation step in ketone precursor. Treating 2,4-difluorobenzaldehyde with BAL presence of thiamin-diphosphate (ThDP) Mg2+ resulted formation α-hydroxy which then underwent preparation 7. innovative not only provides greener alternative but also offers significant advantages over traditional chemical process. Through our efforts development work, have established efficient scalable procedures that enable production 7 moderate 38% yield.

Язык: Английский

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