Article
Chemistry, Physical
Irena Dokli, Nevena Milcic, Petra Marin, Marina Svetec Miklenic, Martina Sudar, Lixia Tang, Zvjezdana Findrik Blazevic, Maja Majeric Elenkov
Summary: The kinetic resolution of a series of fluorinated styrene oxide derivatives using halohydrin dehalogenase was studied. A mutant HheC-W249P showed excellent enantioselectivity in catalyzing nucleophilic ring-opening reactions with azide and cyanide ions, yielding various enantiopure beta-substituted alcohols and epoxides. The enzyme demonstrated tolerance to substrates at concentrations over 50 mM, but different side reactions were observed at elevated concentrations and prolonged reaction times. Bio-catalytic azidolysis and cyanolysis of racemic 4-trifluoromethylstyrene oxide on a preparative scale resulted in the production of specific enantiomers with high yields and enantiomeric excesses.
CATALYSIS COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Christina Jager, Martin Nieger, Kari Rissanen, Jan Deska
Summary: A triple-enzymatic strategy is developed for the direct conversion of γ,δ-unsaturated esters to N-hydroxy-γ-lactam building blocks. This methodology provides a mild and scalable access to N-heterocyclic building blocks and is successfully employed in the synthesis of key intermediates en route to alkaloids of the Cephalotaxus family.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lukas Martin Wingen, Christina Braun, Marvin Rausch, Harald Gross, Tanja Schneider, Dirk Menche
Summary: This article reports detailed information on the design, strategies, and tactics for developing a novel synthetic sequence for farnesyl lipid I and II analogs. The modular route involves a three coupling strategy, including an efficient solid phase synthesis of the elaborate peptide fragment, and is efficiently applied for the convergent synthesis of 3-lipid I and II. Furthermore, the generality of this route is demonstrated by synthesizing 3-lipid I congeners specific to S. aureus and E. faecalis. All 3-lipid I and II building blocks are obtained in high purity with high spectroscopic resolution.
Article
Biochemistry & Molecular Biology
Shunshun Zhou, Jiahui Xiao, Yueyang Ji, Yanfei Feng, Shuqin Yan, Xiufang Li, Qiang Zhang, Renchuan You
Summary: Protein nanofibers derived from natural silk, known as silk nanofibrils (SNFs), are explored as potential biomaterials for tissue engineering scaffolds. In this study, SNF-assembled aerogel scaffolds with biomimetic structure and high water absorbency were developed using a polysaccharides-assisted strategy. The natural polysaccharides were found to regulate SNF assembly, providing the scaffolds with structural stability and tunable mechanical properties. The chitosan-assembled SNF aerogels showed excellent biocompatibility and enhanced cell viability, demonstrating their potential as a bone-mimicking scaffold when functionalized through SNF-mediated biomineralization.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Multidisciplinary
Jie Wang, Jian-Guo Song, Dong-Lin Zhong, Zhi-Zhang Duan, Zi-Jian Peng, Wei Tang, Qiao-Yun Song, Xiao-Jun Huang, Li-Jun Hu, Ying Wang, Wen-Cai Ye
Summary: A synthetic strategy based on biogenetic building blocks has been developed for the biomimetic synthesis of cleistoperlones A-F. The syntheses involve cascade reactions and rare cycloaddition reactions for the construction of complex structures. Cleistoperlone A exhibits significant antiviral activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Johannes Gottschalk, Miriam Assmann, Juergen Kuballa, Lothar Elling
Summary: The study focused on enzymatic synthesis of industrial hyaluronic acid, using immobilized cascade enzymes on magnetic beads to increase productivity and facilitate enzyme recovery. Results showed successful production of high-quality HA in repetitive batches.
Article
Chemistry, Medicinal
Christopher G. Thomson, Kelly Boss, Amy Calhoun, Cary Fridrich, Kevin M. Gardinier, Edward C. Hall, Keith Jendza, Louise Kirman, Nancy Labbe-Giguere, Kurt Laumen, Ming Qian, Sanjit Sanyal, Michael D. Shultz, Radka Snajdrova, Kian Tan, Kate Yaping Wang, Fan Yang, Feng Gao, Tao Hong, Elena Dale, Brent Kuzmiski, Danny Ortuno, Daniel S. Palacios
Summary: We have developed a chiral synthesis route for muscarinic M4 agonists, enabled by the biocatalytic synthesis of key spirocyclic diamine building blocks. The bifunctional compounds were used to optimize a synthetic sequence toward advanced intermediates for further exploration. These intermediates were then utilized for early medicinal chemistry and identification of selective M1/M4 agonists.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Yan-Long Yang, Man Zhou, Lin Yang, Markus Gressler, Johannes Rassbach, Jacob M. Wurlitzer, Ying Zeng, Kun Gao, Dirk Hoffmeister
Summary: In this study, the genetic locus responsible for the biosynthesis of panepoxydone in the basidiomycete mushroom Panus rudis was identified. The cytochrome P450 enzyme PanH was characterized as the catalyst for epoxide formation in this pathway. The study also demonstrated the ability to synthesize bioactive epoxycyclohexenone compounds using a PanH-producing yeast as a biocatalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chao Shou, Yu-Cong Zheng, Jing-Ru Zhan, Chun-Xiu Li, Jian-He Xu
Summary: A new method has been developed for microbial synthesis of plant-based (-)-menthol, with significantly increased production by replacing inefficient enzymes from Mentha piperita. This lays a reliable foundation for the microbial synthesis of (-)-menthol.
Article
Chemistry, Multidisciplinary
Yongwei Zhao, Edward Marschall, Maxine Treisman, Alasdair McKay, Leo Padva, Max Crusemann, David R. Nelson, David L. Steer, Ralf B. Schittenhelm, Julien Tailhades, Max J. Cryle
Summary: This study investigates the use of peptide crosslinking cytochrome P450 enzymes in generating cyclic tripeptides from simple synthons. The enzymes produced both tyrosine-histidine and tyrosine-tryptophan crosslinked tripeptides, the latter being a rare example of phenolic crosslinking to an indole moiety. The tripeptides can be easily isolated after removing the leader peptide and can include a wide range of amino acids. This research suggests that P450 enzymes have the potential to play a significant role in the synthesis of high-value cyclic tripeptides, which can be further diversified using selective chemical techniques.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Daniel J. Foley, Herbert Waldmann
Summary: Natural product-inspired compound collections are important sources for discovering new bioactive compounds for treating diseases. Ketones, with their variety of synthetic transformations, prevalence as commercial building blocks, and relative ease of synthesis, can be valuable as starting materials for the synthesis of natural product-inspired compounds. This review explores the use of ketones as general precursors and summarizes the synthetic transformations available for the annulation of natural product ring-systems to ketone starting materials.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Yu Tian, Xi-Tao Li, Ji-Ren Liu, Jian Cheng, Ang Gao, Ning-Yuan Yang, Zhuang Li, Kai-Xin Guo, Wei Zhang, Han-Tao Wen, Zhong-Liang Li, Qiang-Shuai Gu, Xin Hong, Xin-Yuan Liu
Summary: The study demonstrates an enantioconvergent radical C(sp(3))-S cross-coupling reaction using chiral tridentate anionic ligands and Cu(I) catalysts. This method provides a broad substrate scope, high enantioselectivity, and access to useful alpha-chiral alkyl organosulfur compounds with different sulfur oxidation states, serving as a complementary approach to known asymmetric C(sp(3))-S bond formation methods.
Article
Engineering, Multidisciplinary
Jianhua Wang, Kai Li, Yaojia He, Xiaoxiao Liu, Pengbo Wang, Li Xu, Jinyong Yan, Yunjun Yan
Summary: Inspired by the self-assembly of small biomolecules, a new method of constructing metal-matrix composites by self-assembly of Mn2+-induced L-cystine to immobilize enzymes has been developed for advanced enzyme engineering. The study shows that protein molecules can directly participate in the coordinated self-assembling process, and a two-enzyme directed self-assembled system has been employed for the cascade reaction in fast transforming soybean oil into fatty acid hydroperoxides.
COMPOSITES PART B-ENGINEERING
(2021)
Article
Chemistry, Applied
Wenjuan Feng, Ziqi Wang, Tao Zhang, Osvaldo H. Campanella, Ming Miao
Summary: A maltodextrin-derived dendritic nanoparticle with controllable structure was fabricated using microbial branching enzyme, and its structural characterizations were investigated. The enzyme-catalyzed product exhibited a tighter and more compact branched structure with larger size, higher molecular density, and a higher percentage of alpha-1,6 linkage compared to the maltodextrin substrate. The interaction between a molecular rotor and the dendrimer structure confirmed the presence of numerous nano-pockets at the branch points of the nanoparticle.
CARBOHYDRATE POLYMERS
(2023)
Review
Chemistry, Organic
Yulia A. Trukhanova, Nikita M. Chernov, Elena V. Kuvaeva, Igor P. Yakovlev
Summary: This article comprehensively reviews the progress in C,N-diarylformamidine chemistry and covers the research findings from 1999 to 2022. The research indicates that synthesizing complex molecules through the modification of C,N-diarylformamidine compounds can potentially expand the range of drugs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)