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Pseudouridine-Modifying Enzymes SapB and SapH Control Entry into the Pseudouridimycin Biosynthetic Pathway.
ACS Chem Biol
April 2023
Department of Life Technologies, University of Turku, FIN-20014 Turku, Finland.
Pseudouridimycin is a microbial -nucleoside natural product that specifically inhibits bacterial RNA polymerases by binding to the active site and competing with uridine triphosphate for the nucleoside triphosphate (NTP) addition site. Pseudouridimycin consists of 5'-aminopseudouridine and formamidinylated, N-hydroxylated Gly-Gln dipeptide moieties to allow Watson-Crick base pairing and to mimic protein-ligand interactions of the triphosphates of NTP, respectively. The metabolic pathway of pseudouridimycin has been studied in species, but no biosynthetic steps have been characterized biochemically.
View Article and Find Full Text PDFCharacterization of the Oxazinomycin Biosynthetic Pathway Revealing the Key Role of a Nonheme Iron-Dependent Mono-oxygenase.
J Am Chem Soc
June 2022
Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
Oxazinomycin is a -nucleoside natural product with antibacterial and antitumor activities. In addition to the characteristic -glycosidic linkage shared with other -nucleosides, oxazinomycin also features a structurally unusual 1,3-oxazine moiety, the biosynthesis of which had previously been unknown. Herein, complete in vitro reconstitution of the oxazinomycin biosynthetic pathway is described.
View Article and Find Full Text PDFDivergent Biosynthesis of C-Nucleoside Minimycin and Indigoidine in Bacteria.
iScience
December 2019
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education, and School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China. Electronic address:
Minimycin (MIN) is a C-nucleoside antibiotic structurally related to pseudouridine, and indigoidine is a naturally occurring blue pigment produced by diverse bacteria. Although MIN and indigoidine have been known for decades, the logic underlying the divergent biosynthesis of these interesting molecules has been obscure. Here, we report the identification of a minimal 5-gene cluster (min) essential for MIN biosynthesis.
View Article and Find Full Text PDFMedicinal chemistry of oxazines as promising agents in drug discovery.
Chem Biol Drug Des
January 2020
Department of Pharmacy, Faculty of Health Sciences, Muhammadiyah University of Palangkaraya, Palangka Raya, Indonesia.
Oxazines have brought much synthetic interest due to their extensive biological activities. These are the important category of heterocycles, which may be formally derived from benzene and its reduction products by convenient substitution of carbon (and hydrogen) atoms by nitrogen and oxygen. In the last few decades, oxazine derivatives have documented as worthy synthetic intermediates and also blessed with notable sedative, analgesic, anticonvulsant, antipyretic, antimicrobial, antitubercular, antimalarial, antioxidant, and anticancer activities.
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