Review
Biochemical Research Methods
Felix Kaspar, Anett Schallmey
Summary: Enzymes are recognized as valuable tools in synthetic chemistry, enabling transformations that conventional organochemical approaches cannot achieve. Their expanding role in biocatalysis has introduced new opportunities for synthetic strategies and retrosynthetic disconnections. This review highlights recent literature examples to demonstrate the strategic uses of enzymes in natural product synthesis and advocates for their inclusion in the standard repertoire for complex small-molecule synthesis.
CURRENT OPINION IN BIOTECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Zefei Xu, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: A general chemo-enzymatic approach for the efficient asymmetric synthesis of chiral 3-substituted tetrahydroquinolines has been developed, combining biocatalysis and the Buchwald-Hartwig cross-coupling reaction. The method involves a one-pot ene reductase (ERED)/imine reductase (IRED) cascade and successfully addresses the issue of racemization of the intermediate. This method offers a practical strategy for the construction of chiral 3-substituted tetrahydroquinolines.
Review
Chemistry, Organic
Samata E. Shetgaonkar, Fateh V. Singh
Summary: Hypervalent iodine catalysis is a fast-growing field in hypervalent iodine chemistry. Recent research has focused on the discovery of new chiral hypervalent iodine catalysts and their application in stereoselective reactions. These catalysts have been successful in achieving high enantiomeric excess in various organic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Li Ling, Zeli Song, He Shan, Chao Wang, Shouting Li, Yanjiao Wang, Jianfeng Hu, Qian Chen, Hao Zhang, Yong Yang
Summary: A series of planar chiral indene-fused ferrocenes were successfully synthesized with excellent yields (up to 99%) and high enantioselectivities (up to 99% ee) through intramolecular asymmetric C-H arylation. These compounds were then transformed to chiral ferrocenyl phosphines, featuring both planar and central chiralities, in good yields (up to 83%) and excellent diastereoselectivities (up to 99% de) through diastereoselective phosphination. The newly developed ligands demonstrated potential applications in a Pd-catalyzed enantioselective allylic alkylation reaction with high enantioselectivity (92% ee) and good yield (89%).
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Tobias M. Milzarek, Tobias A. M. Gulder
Summary: This article describes the first total synthesis of fungal sorbicillinoids spirosorbicillinols A-C, with a key step being a Diels-Alder cycloaddition reaction. The work provides a method for synthesizing all natural spirosorbicillinols and unnatural diastereomers.
COMMUNICATIONS CHEMISTRY
(2023)
Review
Chemistry, Organic
Gerardo H. Morales-Monarca, Dino Gnecco, Joel L. Teran
Summary: This Review provides a comprehensive overview of the chemistry of N-acyl-1,3-oxazolidines, highlighting their versatile applications in asymmetric synthesis and the synthesis of bioactive molecules and natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Agricultural Engineering
Lei Gong, Yuansong Xiu, Jinjun Dong, Ruizhi Han, Guochao Xu, Ye Ni
Summary: A feasible chemo-enzymatic procedure was developed using a combination of magnetic solid acid catalyst and immobilized cell biocatalyst for synthesizing noncanonical amino acids from renewable biomass feedstocks.
BIORESOURCE TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Karolina Kaminska, Elzbieta Wojaczynska
Summary: This paper describes the synthesis of chiral diselenides based on 2-azabicycloalkane or the pyrrolidine skeleton using in situ generated Na2Se2 as an efficient selenylating reagent. All the diselenides were obtained in moderate yields under mild conditions. The well-defined enantio- and diastereomerically pure compounds were tested in the asymmetric alkoxyselenylation of alkenes yielding products with diastereoisomeric excess up to >99%.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Wanlong Xiao, Yuhao Mo, Jing Guo, Zhishan Su, Shunxi Dong, Xiaoming Feng
Summary: Chiral macrodiolides with 16, 18, or 20-membered rings were successfully synthesized with high diastereoselectivities and excellent enantioselectivities by adjusting the tether length at the C3 position of indoles. Density functional theory calculations indicated the formation of macrocycles was more favorable than that of 9-membered-ring lactones in terms of kinetics and thermodynamics. The potential utility of these chiral macrodiolide molecules was demonstrated in enantiomeric recognition of aminols and chemical recognition of metal ions.
Article
Multidisciplinary Sciences
J. Miguel Carceller, Karen S. Arias, Maria J. Climent, Sara Iborra, Avelino Corma
Summary: Valuable chiral amines have been selectively synthesized from renewable carbonyl compounds through a two-step semicontinuous process using a combination of chemical and enzymatic catalysts. The enzymatic catalyst, supported on a zeolite, enables the conversion of prochiral ketones into chiral amines. The process has been demonstrated to produce industrially relevant chiral amines with high yields and enantiomer excess.
NATIONAL SCIENCE REVIEW
(2022)
Article
Chemistry, Multidisciplinary
Vanessa Harawa, Thomas W. Thorpe, James R. Marshall, Jack J. Sangster, Amelia K. Gilio, Lucian Pirvu, Rachel S. Heath, Antonio Angelastro, James D. Finnigan, Simon J. Charnock, Jordan W. Nafie, Gideon Grogan, Roger C. Whitehead, Nicholas J. Turner
Summary: The development of efficient and sustainable methods for the synthesis of nitrogen heterocycles is a key goal for the chemical industry. This study presents a chemo-enzymatic approach for the synthesis of substituted piperidines, combining chemical synthesis and biocatalysis. This approach has proven useful for the synthesis of antipsychotic drugs and important intermediates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Kazem Mahmoudzadeh, Zohreh Habibi, Maryam Yousefi, Mostafa Mostafavi, Mehdi Mohammadi
Summary: Increasing attention has been given to peptides as potential therapeutics, leading to the search for new peptide synthetic approaches and modifications. Enzymes have recently gained attention as a novel strategy and powerful tool for peptide and protein ligation. This study presents a fully convergent chemoenzymatic peptide synthesis process for the synthesis of aviptadil, a therapeutic peptide, using different peptiligase variants in aqueous environments.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Multidisciplinary
Gaikwad Rajendra, Krithika Ganesh, G. Govinda Rajulu, Ganesh Sambasivam, Ramaraj Selvaraj, G. Charan Kumar, Shashank C. Ravikumar, Prajwal C. Acharya, Nagashree Shivashankarappa
Summary: A facile, chemo-enzymatic one-pot and scalable procedure was developed for the synthesis of the key chiral intermediate of pralsetinib in an aqueous micellar medium. The method achieved high enantioselectivity without the use of expensive chiral ligands and toxic reagents. A green synthesis of chiral intermediate of pralsetinib was carried out using an enzyme ATA-260 in an aqueous media with >99.9 % ee that was confirmed by a chiral reverse-phase HPLC.
Article
Chemistry, Multidisciplinary
Junyang Dong, Jianfeng Hu, Hao Zhang
Summary: This article presents an efficient method for the synthesis of ferrocenyl dithiocarbamate derivatives under green conditions, using a simple condensation reaction between dithiocarbamate and N-tosylhydrazone. The method is metal-free, offering high yields and good functional group tolerance. Additionally, compound 3e demonstrates excellent recognition of Cu2+ using optical and electrochemical methods, with a detection limit of 5.31 x 10(-7) M.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Bing Chen, Damian Padin, Charlotte. N. N. Stindt, Ben. L. L. Feringa
Summary: In this paper, a novel strategy for the stereocontrolled synthesis of versatile chiral P-stereogenic alkenylphosphonamidates is reported. This strategy involves a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. The reaction conditions were found to exhibit chemo- and diastereodivergent behavior, and the chiral alkenylphosphonamidates obtained can be selectively derivatized for the synthesis of structurally diverse P-stereogenic compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
