Manganese/Enzyme Sequential Catalytic Pathway for the Production of Optically Active γ-Functionalized Alcohols DOI
Meng Deng, Jiaqi Yang, Z.-G. Kong

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9103 - 9109

Published: June 6, 2024

A brief, practical catalytic process for the production of optically active γ-functionalized alcohols from relevant alkenes has been developed by using a robust Mn(III)/air/(Me2SiH)2O system combined with lipase-catalyzed kinetic resolution. This approach demonstrates exceptional tolerance toward proximal functional groups present on alkenes, enabling achievement high yields and exclusive enantioselectivity. Under this sequential system, chiral alkene precursors can also be converted into related acetates as separable single enantiomers.

Language: Английский

Iron Heme Enzyme-Catalyzed Cyclopropanations with Diazirines as Carbene Precursors: Computational Explorations of Diazirine Activation and Cyclopropanation Mechanism DOI
Torben Rogge, Qingyang Zhou, Nicholas J. Porter

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(5), P. 2959 - 2966

Published: Jan. 25, 2024

The mechanism of cyclopropanations with diazirines as air-stable and user-friendly alternatives to commonly employed diazo compounds within iron heme enzyme-catalyzed carbene transfer reactions has been studied by means density functional theory (DFT) calculations model systems, quantum mechanics/molecular mechanics (QM/MM) calculations, molecular dynamics (MD) simulations the cyclopropanation transition state in enzyme active site. reaction is initiated a direct diazirine-diazo isomerization occurring site enzyme. In contrast, an proceeding via formation free intermediate lieu direct, one-step process was observed for systems. Subsequent benzyl acrylate takes place through stepwise C–C bond diradical intermediate, delivering cyclopropane product. origin diastereo- enantioselectivity investigated MD simulations, which indicate preferred cis-cyclopropane steric control.

Language: Английский

Citations

14

One-pot chemo- and photo-enzymatic linear cascade processes DOI Creative Commons
J. M. Carceller, Karen S. Arias, María J. Climent

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(15), P. 7875 - 7938

Published: Jan. 1, 2024

This review explores linear cascade reactions by combining chemo-, photo- and biocatalysts for organic synthesis strategies to overcome incompatibility issues.

Language: Английский

Citations

10

Chemoenzymatic synthesis of macrocycles via dynamic kinetic resolution of secondary alcohols DOI

Javier Guerrero‐Morales,

Marie Scaglia,

Edouard Fauran

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(10), P. 1275 - 1282

Published: July 2, 2024

Language: Английский

Citations

5

Co-immobilization of enzymes and chemocatalysts for one-pot chemoenzymatic cascades: Scaffold engineering toward more efficient catalysis DOI Creative Commons
Tianyou Chen,

Yizhuo Lu,

Xiaorong Xiong

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(3), P. 100894 - 100894

Published: Jan. 21, 2024

Language: Английский

Citations

4

Merging High‐Pressure Syngas Metal Catalysis and Biocatalysis in Tandem One‐Pot Processes for the Synthesis of Nonchiral and Chiral Alcohols from Alkenes in Water DOI Creative Commons

Hannah Bork,

Kim E. Naße,

Andreas J. Vorholt

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 17, 2024

While simultaneously proceeding reactions are among the most fascinating features of biosynthesis, this concept tandem processes also offers high potential in chemical industry terms less waste production and improved process efficiency sustainability. Although examples one-pot chemoenzymatic syntheses exist, combination completely different reaction types is rare. Herein, we demonstrate that extreme "antipodes" "worlds catalysis", such as syngas-based high-pressure hydroformylation biocatalyzed reduction, can be combined within a tandem-type water. No significant deactivation was found for either biocatalyst or chemocatalyst. A proof-of-concept starting from 1-octene established with >99 % conversion 80 isolated yield desired alcohol isomers. All necessary components biocatalysis were added to reactor beginning. This has been extended enantioselective synthesis chiral products by conducting styrene an enzymatic dynamic kinetic resolution mode, leading excellent enantiomeric ratio 91 : 9 (S)-2-phenylpropanol. The overall runs water under mild energy-saving conditions, without any need intermediate isolation.

Language: Английский

Citations

4

Waste Valorization in a Sustainable Bio‐Based Economy: The Road to Carbon Neutrality DOI Creative Commons
Roger A. Sheldon

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 6, 2024

Abstract The development of sustainable chemistry underlying the quest to minimize and/or valorize waste in carbon‐neutral manufacture chemicals is followed over last four five decades. Both chemo‐ and biocatalysis have played an indispensable role this odyssey. particular developments protein engineering, metagenomics bioinformatics preceding three decades a crucial supporting facilitating widespread application both whole cell cell‐free biocatalysis. pressing need, driven by climate change mitigation, for drastic reduction greenhouse gas (GHG) emissions, has precipitated energy transition based on decarbonization defossilization organic production. latter involves biomass CO 2 as feedstock green electricity generated using solar, wind, hydroelectric or nuclear energy. use polysaccharides feedstocks will underpin renaissance carbohydrate with pentoses hexoses base bio‐based solvents polymers environmentally friendly downstream products. availability inexpensive solar led increasing attention electro(bio)catalysis photo(bio)catalysis which turn leading myriad innovations these fields.

Language: Английский

Citations

4

Merging Au(I)-Catalysis and Biocatalysis: Practical and Scalable Synthesis of Chiral Amino Building Blocks from Alkynes DOI

Meriem Daghmoum,

Nazarii Sabat,

Meije Lecoq

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2484 - 2491

Published: Jan. 27, 2025

Au(I)-catalyzed hydration of aliphatic terminal alkynes is followed by transaminase-catalyzed reductive amination, leading to enantioenriched chiral amines. The approach features a one-pot reaction with no particular need for compartmentalization strategy. Final functionalization performed in situ leads variety amines, pyrroles, and 1-pyrrolines obtained high enantioselectivities. method demonstrates applicability the synthesis bioactive drugs such as clobenzorex (43% yield, 3 steps, 96% ee) precursor lisdexamfetamine (34% dr 98:2).

Language: Английский

Citations

0

Host–guest chemistry on living cells enabling recyclable photobiocatalytic cascade DOI Creative Commons
Jiaheng Zhang, Vasco F. Batista, René Hübner

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: 16(10), P. 4480 - 4489

Published: Jan. 1, 2025

Combining chemical and whole-cell catalysts enables sustainable chemoenzymatic cascade reactions. However, their traditional combination faces challenges in catalyst recycling maintaining cell viability. Here, we introduce a supramolecular host-guest strategy that efficiently attaches photocatalysts to bacterial cells, facilitating recyclable photobiocatalysis. This method involves attaching cationic polyethylenimine (PEI) polymer, functionalized with β-cyclodextrin (β-CD), E. coli cells. The polymer attachment is biocompatible protective, safeguarding the cells from harsh conditions such as UV radiation organic solvents, without causing death. Additionally, presence of β-CD imparts plug-and-play capability enabling straightforward integration guest - specifically anthraquinone onto surface through interactions. effective cellular promotes efficient photobiocatalytic cascades supports photocatalyst's reuse. system thus represents promising platform for advancing photobiocatalysis synthesis.

Language: Английский

Citations

0

Chemoenzymatic synthesis DOI Creative Commons
Paweł Borowiecki, Sandy Schmidt

Communications Chemistry, Journal Year: 2025, Volume and Issue: 8(1)

Published: March 13, 2025

Communications Chemistry is pleased to introduce a Collection of research works focused on recent developments within the interdisciplinary field chemoenzymatic synthesis. Here, Guest Editors highlight key themes and look towards future this field.

Language: Английский

Citations

0

Modular Chemoenzymatic Cascade for Highly Diastereo- and Enantioselective Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines DOI
Honghui Zhang, Yan Zhang,

Changtong Zhu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5426 - 5434

Published: March 18, 2025

Language: Английский

Citations

0