Kinetic Resolution of Cyclic Tertiary Alcohols with Lipase A from Candida Antarctica DOI

Satoshi Horino,

Karla Wagner,

Anke Hummel

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(21)

Published: April 2, 2024

Abstract Enzyme‐catalyzed acylative kinetic resolution (KR) and dynamic (DKR) of racemic primary secondary alcohols have been widely reported to produce esters with high enantiomeric purity. In contrast, similar KRs tertiary for only a limited range substrates require prolonged reaction times several days. To gain deeper insight into the substrate scope increase process efficiency, we examined conditions using commercially available immobilized lipase A from Candida antarctica found that addition heterogeneous, inorganic base sodium carbonate significantly increased rate while maintaining enantioselectivity. The use vinyl hexanoate as acyl donor provided were stable during chromatography purification. optimized then successfully applied cyclic containing tetralin, dihydroindene, chromane, thiochromane skeletons having, in part, substituent on aromatic ring. this study structure–reactivity relationship enzymatic KR‐type reactions, achieved >30 % conversion various 24 h at 25 °C, producing optically active 88–99 ee.

Language: Английский

From nature to industry: Harnessing enzymes for biocatalysis DOI
Rebecca Buller, Stefan Lutz, Romas J. Kazlauskas

et al.

Science, Journal Year: 2023, Volume and Issue: 382(6673)

Published: Nov. 23, 2023

Biocatalysis harnesses enzymes to make valuable products. This green technology is used in countless applications from bench scale industrial production and allows practitioners access complex organic molecules, often with fewer synthetic steps reduced waste. The last decade has seen an explosion the development of experimental computational tools tailor enzymatic properties, equipping enzyme engineers ability create biocatalysts that perform reactions not present nature. By using (chemo)-enzymatic synthesis routes or orchestrating intricate cascades, scientists can synthesize elaborate targets ranging DNA pharmaceuticals starch made vitro CO2-derived methanol. In addition, new chemistries have emerged through combination biocatalysis transition metal catalysis, photocatalysis, electrocatalysis. review highlights recent key developments, identifies current limitations, provides a future prospect for this rapidly developing technology.

Language: Английский

Citations

224
Salient Achievements in Synthetic Organic Chemistry Enabled by Mechanochemical Activation DOI
Eusebio Juaristi, C.G. Ávila-Ortíz

Synthesis, Journal Year: 2023, Volume and Issue: 55(16), P. 2439 - 2459

Published: May 3, 2023

Abstract Although known for millennia, it is only recently that mechanochemistry has received serious attention by chemists. Indeed, during the past 15 years an extraordinary number of reports concerning solid-state chemical transformations through grinding and milling techniques have been recorded. This short review discusses circumstances led this renaissance, highlighting present intense interest in so-called green chemistry, enabling capacity to handle insoluble substrates, identification profound influence additives can on mechanochemically activated reactions. The core account focuses salient developments synthetic organic especially amino acid peptide­ mechanosynthesis, successful employment mechanochemical activation combination with asymmetric organocatalysis, promising enzymatic whole cell biocatalysis, remarkable achievement multicomponent selective reactions via complex, multistep reaction pathways, mechanosynthesis representative heterocycles. final section comments some pending tasks area, such as scaling-up processes be practical use industry, requirement easier more efficient control parameters monitoring devices, consequently careful analysis additional procedures a proper understanding phenomena. 1 Introduction 2 Brief History Mechanochemistry 3 Milling Equipment Reaction Parameters 4 Attributes That Propelled Its Present Renaissance 4.1 Enormous Attention Being Presently Paid Sustainable Chemistry 4.2 Reduced Energy Consumption 4.3 Additive-Based 4.4 Handling Insoluble Reactants 4.5 ‘Impossible’ Reactions Are Successful 4.6 Air- Water-Sensitive Reagents Ball 5 Salient Developments Mechanochemical Activation Synthetic Organic 5.1 Amino Acid Peptide Mechanosynthesis 5.2 Asymmetric Synthesis Organocatalysis under Ball-Milling Conditions 5.3 Mechanoenzymology 5.4 Multicomponent Activated 5.5 Heterocycles Modification 6 Future Directions 6.1 Scaling-Up Protocols 6.2 Temperature-Controlled 6.3 Understanding Transformations 6.4 Emerging Techniques 7 Conclusions

Language: Английский

Citations

52
Smart chemistry and applied perceptions of enzyme-coupled nano-engineered assemblies to meet future biocatalytic challenges DOI
Ayesha Anwar, Muhammad Imran, Hafiz M.N. Iqbal

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 493, P. 215329 - 215329

Published: July 9, 2023

Language: Английский

Citations

28
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

12
Molecular Engineering and Morphology Control of Covalent Organic Frameworks for Enhancing Activity of Metal‐Enzyme Cascade Catalysis DOI Creative Commons
Hao Zhao, Jialin Zhang, Yunting Liu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(25)

Published: April 23, 2024

Abstract Metal‐enzyme integrated catalysts (MEICs) that combine metal and enzyme offer great potential for sustainable chemoenzymatic cascade catalysis. However, rational design construction of optimal microenvironments accessible active sites in individual nanostructures are necessary but still challenging. Herein, Pd nanoparticles (NPs) Candida antarctica lipase B (CALB) co‐immobilized into the pores surfaces covalent organic frameworks (COFs) with tunable functional groups, affording Pd/COF‐X/CALB (X = ONa, OH, OMe) MEICs. This strategy can regulate microenvironment around NPs CALB, their interactions substrates. As a result, activity COF‐based MEICs catalyzing dynamic kinetic resolution primary amines is enhanced followed COF‐OMe > COF‐OH COF‐ONa. The experimental simulation results demonstrated groups COFs modulated conformation electronic states NPs, affinity to substrate, which contributed improvement catalytic Further, prepared using COF hollow structure as support material, increased mass transfer efficiency, thus improving performance. work provides blueprint preparation highly

Language: Английский

Citations

11
Stereodivergent Protein Engineering of Fatty Acid Photodecarboxylase for Light‐Driven Kinetic Resolution of Sec‐Alcohol Oxalates DOI

Kaihao Mou,

Yue Guo,

Weihua Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(10)

Published: Jan. 10, 2024

Stereodivergent engineering of one enzyme to create stereocomplementary variants for synthesizing optically pure molecules with tailor-made (R) or (S) configurations on an optional basis is highly desirable and challenging. This study aimed engineer fatty acid photodecarboxylase from Chlorella variabilis (CvFAP) using the focused rational iterative site-specific mutagenesis (FRISM) strategy obtain two excellent selectivity (both giving products up 99 % e.e.). These were used CvFAP-catalyzed light-driven kinetic resolution oxalates oxamic acids prepared corresponding sec-alcohols amines, providing a new biotransformation process preparing chiral amines. Molecular dynamics simulation, data transient spectra revealed source selectivity. represents first example amines catalyzed by pair CvFAPs.

Language: Английский

Citations

10
Status check: biocatalysis; its use with and without chemocatalysis. How does the fine chemicals industry view this area? DOI
Fabrice Gallou, Harald Gröger, Bruce H. Lipshutz

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(16), P. 6092 - 6107

Published: Jan. 1, 2023

Stages of the penetration catalytic technology and necessity for fruitful collaboration.

Language: Английский

Citations

19
A review of nanotechnology in enzyme cascade to address challenges in pre-treating biomass DOI
Akhtar Hussain, Fouziya Parveen, Ayush Saxena

et al.

International Journal of Biological Macromolecules, Journal Year: 2024, Volume and Issue: 270, P. 132466 - 132466

Published: May 16, 2024

Language: Английский

Citations

8
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

6
Chemoenzymatic Sequential Catalysis with Carbonic Anhydrase for the Synthesis of Chiral Alcohols from Alkanes, Alkenes, and Alkynes DOI
Zhenzhong Li,

Zicong Wan,

Wei Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8786 - 8793

Published: May 22, 2024

Chiral alcohols are important intermediates for various fine chemicals and pharmaceuticals. Integrating chemical catalysis efficient enzyme in sequential systems the synthesis of chiral is considered an ecofriendly promising approach. Herein, employing a highly selective carbonic anhydrase II different catalysts, we constructed three general chemoenzymatic alcohol compound from alkanes, alkenes, alkynes, respectively. Compared to classical approaches, combination promiscuous simple since it requires only mild reaction conditions avoids expensive ligands cumbersome operation steps. In this integrated approach, wide variety readily available aryl alkynes transformed into valuable with excellent enantioselectivity up 99% (nearly all above 90%). This unified strategy combining enzymatic catalyses advances process powerful transformations.

Language: Английский

Citations

6