Biocatalytic Formal Asymmetric para-Aminoethylation of Unprotected Phenols to Chiral Amines DOI
Jingqi Zhang, Xuan Deng, Xue Han

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 81 - 90

Published: Dec. 13, 2024

Enantiomerically pure amines are vital for the development of biologically active compounds in medicine and agriculture. While aminoalkylation phenols is well-established creating nitrogen-containing frameworks, regio- stereoselective para-aminoethylation unprotected underexplored. To fill this gap, we propose a one-pot cascade biocatalysis system asymmetric into chiral amines, using simple pyruvate, NH4Cl, D/l-alanine as starting materials. Utilizing modular approach, successfully performed through sequential process vinylation hydroamination, achieving good conversions (51.0–72.0%) >99% ee both enantiomers amines. Additionally, biobased p-hydroxycinnamic acid l-tyrosine their derivatives were converted with moderate to (39.4–87%) integrating decarboxylation/hydroamination deamination-decarboxylation/hydroamination. This marks successful de novo biosynthesis method formal phenols.

Language: Английский

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
Perspectives on flow biocatalysis: the engine propelling enzymatic reactions DOI Creative Commons
Ana I. Benítez‐Mateos, Francesca Paradisi

Journal of Flow Chemistry, Journal Year: 2023, Volume and Issue: 14(1), P. 211 - 218

Published: Oct. 23, 2023

Abstract Flow biocatalysis has emerged as an empowering tool to boost the potential of enzymatic reactions towards more automatized, sustainable, and generally efficient synthetic processes. In last fifteen years, increasing number biocatalytic transformations carried out in continuous flow exemplified benefits that this technology can bring incorporate into industrial operations. This perspective aims capture a nutshell available methodologies for well discuss current limitations future directions field. Graphical abstract

Language: Английский

Citations

13
Light-Driven Photobiocatalytic Oxyfunctionalization in a Continuous Reactor System without External Oxygen Supply DOI Creative Commons
Lenny Malihan‐Yap, Qianwei Liang, Alessia Valotta

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2025, Volume and Issue: 13(10), P. 3939 - 3950

Published: March 5, 2025

Oxygenases catalyze C-H oxyfunctionalization under mild reaction conditions and often display outstanding selectivity. However, their utilization is hampered by the difficulty of transporting oxygen across gas-liquid interface, which particularly problematic for continuous reactor systems can only be alleviated high pressure or use complex oxygen-permeable materials. Herein, directly released into medium phototrophic cyanobacterium Synechocystis sp. PCC 6803 expressing genes a Baeyer-Villiger Monooxygenase from Burkholderia xenovorans to drive oxidation cyclohexanone production polymer precursor, ε-caprolactone. The rates at photosynthetic solely were determined performing in coil with very limited external supply. In heterotrophic nonoxygen-producing Escherichia coli same gene, 10-fold lower specific activity was observed when performed compared batch mode underlining impact oxygen-limitation on volumetric productivity. contrast, cyanobacterial whole cells showed activities 16.7 13.5 U gDCW -1 nonoxygen-limited oxygen-limited flow, respectively. Net whole-cell biocatalyst during led steady-state concentration allowing productivities as 3 mmol L-1 h-1 highlighting advantages photoautotrophic oxygen-limiting conditions. Moreover, space-time yield improved 7-fold (2.8 vs 0.4 g h-1) utilizing mode. combination flow catalysis overcome current limitations photo(bio)oxidation achieve significant improvements terms productivity enabling more sustainable chemical synthesis. This approach using whole-cells cyanobacteria achieves notably ratio waste product (E-factor) higher atom economy mediated .

Language: Английский

Citations

0
Cell-free chemoenzymatic cascades with bio-based molecules DOI Creative Commons
Henrik Terholsen, Sandy Schmidt

Current Opinion in Biotechnology, Journal Year: 2023, Volume and Issue: 85, P. 103058 - 103058

Published: Dec. 27, 2023

For the valorization of various bio-based feedstocks, combination different catalytic systems with biocatalysis in chemoenzymatic cascades has been shown to have high potential. However, development such integrated is often limited by catalyst incompatibility. Therefore, incorporating novel concepts into feedstocks currently great interest. This article provides an overview methods/approaches used advance for upgrading feedstocks. It specifically focuses on recent developments enzymes organo- and chemocatalysis. Furthermore, current applications future perspectives integrating as photo- electrocatalysis toward new synthetic routes utilization highly functionalized compounds are reviewed.

Language: Английский

Citations

5
Flow chemistry Set-up Enables Integration of Chemo- and Biocatalysis DOI Creative Commons
Pablo Díaz‐Kruik, Stefania Gianolio, Francesca Paradisi

et al.

CHIMIA International Journal for Chemistry, Journal Year: 2023, Volume and Issue: 77(5), P. 307 - 307

Published: May 31, 2023

The move towards sustainable syntheses is a widespread effort which sees academia and industry developing new strategies solutions. Flow chemistry, in general the flow set up, with compartmentalization of different steps dedicated reactors, offers possibility to integrate biocatalytic within chemical cascade, often without need redesign whole pathway. Here we report key examples field over past few years.

Language: Английский

Citations

4
Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis DOI Creative Commons
Emmanuel Cigan,

Jakob Pletz,

Sarah A. Berger

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(36), P. 9863 - 9871

Published: Jan. 1, 2023

Designing an alternative access to the morphinan scaffold by taking advantage of biocatalysis for asymmetric CN reduction and oxidative C–C bond formation.

Language: Английский

Citations

4
Combined Microbial Fermentation Converts Bioactive Compounds in Nitraria tangutorum Bobrov Fruit and Displays Its Antidiabetic Potential DOI Open Access

Isabelle Fan Yang,

Changhong Liu

Published: March 21, 2024

Nitraria tangutorum Bobrov is a berry shrub with white flowers and red fruits, which grows in the deserts Tibetan Plateau, Mongolia, western China. Its fruit N. (NTF) contains various bioactive compounds, anti-fatigue, anti-inflammatory, neuroprotective functions. However, high saccharide content of NTF makes it unsuitable for diabetic patients. In this study, we fermented to obtain juice (NTJ), residue (NTR), are suitable diabetics consume. We characterized compounds NTF, NTR, NTJ, found that fermentation increased diversity greatly reduced sucrose, glucose, fructose while generating trehalose, has potential manage blood glucose levels. Further, NTJ displays anti-diabetic due properties. This study provides basis further clinical research on NTJ's function humans.

Language: Английский

Citations

1
Solvent Switching in Continuous Multistep Chemoenzymatic Synthesis: Telescoping Enzymatic Synthesis of Chiral, Pyridine-Containing Amines with Cross-Coupling as a Case Study DOI
Pablo Díaz‐Kruik, David Roura Padrosa, Eimear Hegarty

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(7), P. 2683 - 2691

Published: May 21, 2024

Chiral α-(hetero)aryl primary amines are gaining momentum for their biological activities and use as building blocks in more complex molecules. Here we report a continuous chemoenzymatic strategy from 2-acetyl-6-bromopyridine enabled by careful solvent selection phase switching. Combining first biocatalytic transamination reaction performed TsRTA biphasic system flow, with inline Boc-protection Suzuki coupling of (substituted)phenylboronic acid, achieves conversions up to >99% toward tert-butyl (R)-(1-(6-(substituted) phenylpyridin-2-yl)ethyl)carbamate the final product. This not only constitutes an important example combinations flow but also highlights importance design minimize waste (through unreacted substrate recirculation), avoid time intensive workups extractions), achieve product space yield 68 mg L–1 h–1 excellent enantiomeric excess (99% ee).

Language: Английский

Citations

1
Kinetic Model for the Heterogeneous Biocatalytic Reactions Using Tethered Cofactors DOI
Rowan McDonough, Charlotte C. Williams, Carol J. Hartley

et al.

Langmuir, Journal Year: 2024, Volume and Issue: 40(13), P. 6685 - 6693

Published: March 25, 2024

Understanding the mechanism of interfacial enzyme kinetics is critical to development synthetic biological systems for production value-added chemicals. Here, catalysis β-nicotinamide adenine dinucleotide (NAD

Language: Английский

Citations

0
Combined Microbial Fermentation Converts Bioactive Compounds in Nitraria Tangutorum Bobrov Fruit and Displays its Antidiabetic Potential DOI Creative Commons

Isabelle Fan Yang,

Changhong Liub

JSM Biotechnology & Biomedical Engineering, Journal Year: 2024, Volume and Issue: 9(1), P. 1 - 12

Published: March 29, 2024

Nitraria tangutorum Bobrov is a berry shrub with white flowers and red fruits, which grows in the deserts Tibetan Plateau, Mongolia, western China. Its fruit N. Fruit (NTF) contains various bioactive compounds, anti-fatigue, anti-inflammatory, neuroprotective functions. However, high saccharide content of NTF makes it unsuitable for diabetic patients. In this study, we fermented to obtain Fermented Juice (NTJ), Residue (NTR), are suitable diabetics consume. We characterized compounds NTF, NTR, NTJ, found that fermentation increased diversity greatly reduced sucrose, glucose, fructose while generating trehalose, has potential manage blood glucose levels. Further, NTJ displays anti-diabetic due properties. This study provides basis further clinical research on NTJ’s function humans.

Language: Английский

Citations

0