Article
Chemistry, Multidisciplinary
Shuailong Li, Dequan Zhang, Runtong Zhang, Shao-Tao Bai, Xumu Zhang
Summary: This article reports a novel rhodium catalyst that enables highly efficient and selective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes, resulting in valuable chiral cyclopropyl entities. The modified ligand used in this study exhibits superior performance compared to traditional diphosphine ligands in asymmetric catalysis. Gram-scale reactions and subsequent transformations of the products were also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Eleonora Grandi, Fatma Feyza Ozgen, Sandy Schmidt, Gerrit J. Poelarends
Summary: Biocatalytic cascades are a powerful tool for synthesizing complex molecules containing oxygen and nitrogen functionalities. This review highlights recent efforts in the development of multi-step syntheses involving C-O and C-N bond-forming enzymes to produce valuable compounds. The use of engineered enzymes, co-substrate and cofactor recycling strategies, and novel tools such as flow systems and confined nanomaterials are discussed to overcome current challenges in multi-enzymatic reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qi Jin, Jingqi Zhang, Shuangping Huang, Lili Gao, Honghong Chang, Jiandong Zhang
Summary: A novel fully biocatalytic system was developed for the direct stereoselective hydroamination of aryl alkenes to produce chiral amines. The process involves sequential alkene asymmetric hydration catalyzed by hydratase (HD), followed by in situ oxidation of alcohol into ketone by two enantiocomplementary alcohol dehydrogenases (ADHs), and finally, enantioselective transformation of ketone into enantiomerically pure amine by γ-transaminase (TA). This research achievement provides a highly selective, highly atom-economical, green and sustainable method for synthesizing chiral amines from alkenes via formal alkene asymmetric hydroamination.
Article
Chemistry, Organic
Ryan R. G. Barrett, Donald A. Campbell, James L. Gleason
Summary: Ethyl diazepane carboxylate catalyzes the oxy-Cope rearrangement of 4-hydroxy- and 4-alkoxy-1,5-hexadiene-2carboxaldehydes via iminium ion activation, leading to cyclopentane-containing products through intramolecular Michael reaction. The reaction is applicable to various substrates, including cyclic and acyclic ones, and shows tolerance towards vinyl substituent substitution. Substrates with cycloalkane framework undergo net ring expansion/cyclopentannulation with high stereocontrol through chairlike transition states. This reaction expands iminium organocatalysis to the oxy-Cope rearrangement within a complexity-generating cascade transformation.
Article
Chemistry, Multidisciplinary
Daniela M. Carminati, Jonathan Decaens, Samuel Couve-Bonnaire, Philippe Jubault, Rudi Fasan
Summary: An efficient biocatalytic method for high diastereo- and enantioselective synthesis of CHF2-containing trisubstituted cyclopropanes has been developed, showing excellent yield and stereoselectivity. The methodology provides a powerful strategy for the stereoselective synthesis of fluorinated building blocks, as demonstrated by the formal total synthesis of a CHF2 isostere of a TRPV1 inhibitor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Marta Meazza, Ramon Rios
Summary: This study describes the first synthesis of 2-alkenylquinolines from 2-allylquinolines and alpha,beta-unsaturated aldehydes. The reaction exhibits high regioselectivity and enantioselectivity, with a broad tolerance of functionalities in both the enal aromatic ring and the quinoline.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Yuanyuan Zhang, Yaoyu Liang, Xiaodan Zhao
Summary: The enantioselective electrophilic three-component thioarylation of alkenes using chiral selenide catalysis with free phenols as arylating sources has been disclosed. Various chiral phenols were obtained in high regio-, enantio-, and diastereoselectivities. Mechanistic studies showed that the transformation proceeded through carbon nucleophilic attack to give the products rather than the intramolecular rearrangement of phenolic ether intermediates.
Article
Chemistry, Multidisciplinary
Dachang Bai, Fen Wu, Lingna Chang, Manman Wang, Hao Wu, Junbiao Chang
Summary: Here, we have developed an efficient method for the direct generation of difluoromethylated stereocenters through Ale-catalyzed regio- and enantioselective hydrosilylation of gem-difluoroalkenes. This method features readily available starting materials and commercial chiral catalysis, is applicable to a wide range of functional groups, and provides high yield and excellent enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yang Gao, Phil S. Baran
Summary: A new approach to the enantiocontrolled synthesis of alpha-amino ketone derivatives is presented using a decarboxylative acylation strategy. This method yields the desired alpha-amido ketones with good yield and high enantioselectivity when an acyl chloride and an alpha-amido-containing redox-active ester are exposed to a nickel catalyst, chiral ligand, and metal reductant. The reaction has wide substrate scope, scalability, and simplifies the synthesis of known structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biotechnology & Applied Microbiology
Dan-Ping Zhang, Xiao-Ran Jing, Lun-Jie Wu, An-Wen Fan, Yao Nie, Yan Xu
Summary: A highly efficient in vivo biocatalysis system was developed for the selective synthesis of D-amino acids via stereoinversion.
MICROBIAL CELL FACTORIES
(2021)
Article
Chemistry, Multidisciplinary
Hui-Hui Wang, Nan-Wei Wan, Run-Ping Miao, Cheng-Li He, Yong-Zheng Chen, Zhi-Qiang Liu, Yu-Guo Zheng
Summary: We report the discovery of an unusual halohydrin dehalogenase, HHDHamb, which can perform bio-nitration of epoxides under relatively low acidic conditions and extremely low temperatures using nitrite as a nitrating agent. This bio-nitration strategy demonstrates high chemo-, regio-, and enantioselectivity, resulting in the catalytic resolution of various epoxides into enantiopure beta-nitroalcohols. The method also exhibits high reaction efficiency and scalability. The crystal structure of HHDHamb was solved to gain insights into the structural determinants of chemoselectivity control in the bio-nitration reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Christopher W. Lamartina, Cassandra A. Chartier, Sumin Lee, Neel H. Shah, Tomislav Rovis
Summary: Here, a modular peptide ligation methodology is reported, which uses Rh(III) catalysis to couple dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner under mild conditions. The method shows excellent functional group tolerance and a large substrate scope, allowing for the construction of unnatural amino acid residues. This methodology is demonstrated in the synthesis of diastereomeric proteasome inhibitor analogs and the ligation of oligopeptides to construct a polypeptide with an unnatural residue.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Lihao Liao, Xinru Xu, Jieying Ji, Xiaodan Zhao
Summary: In this study, an efficient catalytic asymmetric intermolecular iodinative difunctionalization reaction was reported, which successfully transformed challenging substrates into a variety of iodine-functionalized chiral molecules with excellent control over enantio- and diastereoselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Jiapan Niu, Hongli Wu, Changhao Niu, Genping Huang, Chun Zhang
Summary: A practical palladium and amino acid co-catalyzed hydroarylation of unbiased alkenes has been developed, which can construct isolated chiral Csp(2)-Csp(3) bonds with good regio- and enantioselectivity. The potential synthetic utility of a representative product was wellillustrated by further transformations. Furthermore, the mechanism of this reaction was intensively studied through control experiments and DFT calculations.
Article
Chemistry, Organic
Dina Scarpi, Francesco Bagni, Cristina Faggi, Asier Carral-Menoyo, Enrique Gomez-Bengoa, Ernesto G. Occhiato
Summary: Six- and seven-membered ring-fused, functionalized cyclopentadienes can be obtained in moderate to excellent yields through a cascade process involving various reactions. Depending on the treatment of the crude reaction mixtures, different types of cyclopentadienes can be obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biotechnology & Applied Microbiology
Tianwen Wang, Hui Li, Chen Liang, Shiwei Sun, Ao Liu, Hu Zhu
BIOPROCESS AND BIOSYSTEMS ENGINEERING
(2020)
Article
Chemistry, Physical
Qiuju Zhou, Tianwen Wang, Can Wang, Zheng Wang, Yanan Yang, Pei Li, Ruihua Cai, Meng Sun, Hongyu Yuan, Lei Nie
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
(2020)
Article
Biotechnology & Applied Microbiology
Yi Zhou, Balaji Sundara Sekar, Shuke Wu, Zhi Li
BIOTECHNOLOGY AND BIOENGINEERING
(2020)
Review
Chemistry, Multidisciplinary
Shuke Wu, Radka Snajdrova, Jeffrey C. Moore, Kai Baldenius, Uwe T. Bornscheuer
Summary: Biocatalysis is widely used as an alternative to chemical catalysis in various fields, with enzymes playing a key role in organic synthesis, particularly in the production of chiral compounds for pharmaceuticals and flavors. Biocatalysts are also utilized on a large scale for the production of specialty and bulk chemicals. This review focuses on scalable chemical production using enzymes, discussing opportunities, limitations, and emerging enzyme classes through illustrative examples.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sascha Grobe, Christoffel P. S. Badenhorst, Thomas Bayer, Emil Hamnevik, Shuke Wu, Christoph W. Grathwol, Andreas Link, Sven Koban, Henrike Brundiek, Beatrice Grossjohann, Uwe T. Bornscheuer
Summary: In this study, the cytochrome P450 monooxygenase CYP107D1 was engineered for the stereo- and regioselective 7 beta-hydroxylation of lithocholic acid to yield ursodeoxycholic acid. By identifying specificity-determining residues and utilizing a synthetic small library, a nearly perfectly regio- and stereoselective triple mutant was developed, which produces UDCA at significantly higher levels than the initial variant. This biocatalyst offers new possibilities for environmentally friendly synthesis of UDCA from biological waste product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Microbiology
Lei Nie, Ruijiao Zhang, Linfang Zhang, Mengyuan Ma, Congcong Li, Yi Zhang, Yafei An, Hongju Xu, Sa Xiao, Tianwen Wang
Summary: This study successfully used ribosome engineering to induce a stable keratinase overproducer mutant in Bacillus thuringiensis, leading to enhanced keratinase synthesis capacity in liquid LB medium. Genome-wide analysis showed that the phenotypic changes were a result of genetic variations in regulatory regions and non-coding RNA genes, rather than mutations in the commonly recognized hotspot of the rpsL gene.
ARCHIVES OF MICROBIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Chao Xiang, Shuke Wu, Uwe T. Bornscheuer
Summary: By performing directed evolution, a new enzyme variant VF-8M-E with significantly increased specific activity was obtained, which was successfully utilized to produce the key chiral amine intermediate in enantiopure form for Apremilast, representing a new enzymatic approach towards the synthesis of Apremilast.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Tianwen Wang, Chen Liang, Sha Xiao, Li Li, Hongju Xu, Yafei An, Mengyuan Zheng, Lu Liu
Summary: The study investigated the biochemical and enzymological properties of a feather-degrading Bacillus thuringensis produced keratinase, revealing it as an acidic serine protease with optimal activity at 50℃ and pH 6.2, while showing high resistance to Al3+. The enzyme's structure and activity were influenced by ions, and it exhibited unique biochemical properties including activation by Mn2+ and DMSO at low concentrations.
PROTEIN AND PEPTIDE LETTERS
(2021)
Article
Multidisciplinary Sciences
Shuke Wu, Chao Xiang, Yi Zhou, Mohammad Saiful Hasan Khan, Weidong Liu, Christian G. Feiler, Ren Wei, Gert Weber, Matthias Hohne, Uwe T. Bornscheuer
Summary: This study reports a simple, high-throughput, and low-equipment dependent growth selection system for improving the performance of three enzymes in the synthesis of chiral amines. The results show that this system can successfully enhance the specific activity of enzymes, providing a flexible tool for the engineering process.
NATURE COMMUNICATIONS
(2022)
Review
Biochemistry & Molecular Biology
Wei Zhang, Tianwen Wang
Summary: Proteins are crucial biomacromolecules that execute genetic information stored in DNA. Therefore, studying proteins is a central task in biological sciences. The complexity, diversity, and dynamics of protein structure, function, and their relationship, along with the fragility of protein structure, make protein research challenging. This paper reviews the progress in studying protein function, with an emphasis on the impact of high-throughput DNA sequencing and bioinformatics analysis in revolutionizing biological research.
PROTEIN AND PEPTIDE LETTERS
(2023)
Review
Biochemistry & Molecular Biology
Wei Zhang, Kun Liu, Fang Kong, Tao Ye, Tianwen Wang
Summary: Ectoine and its derivative 5-hydroxyectoine are compatible solutes found in the hyperhalophilic bacterium Ectothiorhodospira halochloris from the Egyptian desert. Ectoine serves as a cytoprotectant against harsh conditions and has multiple functions in bacterial and other types of cells. These properties make ectoine attractive for scientific research and industries such as food/agricultural, cosmetic, and therapeutic agent preparation. This article discusses the functions, applications, and advances in ectoine and 5-hydroxyectoine production.
MOLECULAR BIOTECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Chatcha Saengsen, Orawan Sookbampen, Shuke Wu, Sasikarn Seetasang, Wichitpan Rongwong, Litavadee Chuaboon
Summary: This work presents a novel strategy for detecting and purifying levulinic acid and bio-compounds using ion/ligand chromatography and high-performance liquid chromatography techniques. The LC-MS/MS approach shows higher sensitivity in detecting levulinic acid and hydroxymethylfurfural. The purification of levulinic acid from the hydrolysis reaction of cellulose was successfully achieved by optimizing HPLC conditions.
Review
Chemistry, Multidisciplinary
Yi Zhou, Shuke Wu, Uwe T. Bornscheuer
Summary: Developing (chemo)enzymatic cascades for green synthesis is attractive due to streamlining multistep synthetic processes. Recent research focuses on using renewable bio-based resources as starting materials to synthesize high-value compounds from readily available carbohydrate sources.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Dong Yi, Thomas Bayer, Christoffel P. S. Badenhorst, Shuke Wu, Mark Doerr, Matthias Hoehne, Uwe T. Bornscheuer
Summary: Biocatalysis has made revolutionary progress in the past century, benefiting from the integration of multidisciplinary technologies and the development of robust biocatalysts through protein engineering. The network of natural enzymatic synthesis pathways and artificially designed enzymatic cascades have been gradually constructed. Future development will move towards the integration of new technologies, intelligent manufacturing, and enzymatic total synthesis.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
M. Eng. Qingyun Tang, Christoph W. Grathwol, Askin S. Aslan-uzel, Shuke Wu, Andreas Link, Ioannis V. Pavlidis, Christoffel P. S. Badenhorst, Uwe T. Bornscheuer
Summary: Biocatalytic alkylations play a crucial role in obtaining chemo-, regio- and stereoselectively alkylated compounds. Recent research has shown that a halide methyltransferase from Chloracidobacterium thermophilum can synthesize SAM, leading to the development of a method for directed evolution of an HMT from Arabidopsis thaliana and identification of a variant that can produce various SAM analogs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
