Daptomycin, a macrocyclic antibiotic, is here used as a new chiral selector in preparation of chiral stationary phase (CSP) in a recently prepared polymer monolithic capillary. The latter is prepared using the copolymerization of the monomers glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in the presence of daptomycin in water. Under reversed phase conditions (RP), the prepared capillaries were tested for the enantioselective nanoliquid chromatographic separation of fifty of the racemic drugs of different pharmacological groups, such as adrenergic blockers, H1-blockers, NSAIDs, antifungal drugs, and others. Baseline separation was attained for many drugs under RP-HPLC. Daptomycin expands the horizon of chiral selectors in HPLC.
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http://dx.doi.org/10.3390/molecules26123527 | DOI Listing |
The mycomembrane of mycobacteria has long been regarded as the primary barrier to the accumulation of molecules within these bacteria. Understanding accumulation beyond the mycomembrane of ( ) is crucial for developing effective antimycobacterial agents. This study investigates two design principles commonly found in natural products and mammalian cell-permeable peptides - backbone -methylation and macrocyclization - aimed at enhancing accumulation.
View Article and Find Full Text PDFMicrob Cell Fact
January 2025
Chair of Technical Biochemistry, Technische Universität Dresden, Bergstraße 66, 01069, Dresden, Germany.
Background: The biosynthesis of the natural product family of the polycyclic tetramate macrolactams (PoTeMs) employs an uncommon iterative polyketide synthase/non-ribosomal peptide synthetase (iPKS/NRPS). This machinery produces a universal PoTeM biosynthetic precursor that contains a tetramic acid moiety connected to two unsaturated polyene side chains. The enormous structural and hence functional diversity of PoTeMs is enabled by pathway-specific tailoring enzymes, particularly cyclization-catalyzing oxidases that process the polyene chains to form distinct ring systems, and further modifying enzymes.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
There has been a long search for a simple preparation of new cyclic analogues of ionophore antibiotics. We report a simple and general synthesis of three new cyclic derivatives of polyether ionophore, monensin A (MON). The application of the Huisgen 1,3-dipolar cycloaddition of azides and terminal alkynes to macrocyclization results in a concise, synthetic route to monensin lacton or lactam in only 4 steps.
View Article and Find Full Text PDFInorg Chem
January 2025
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, P. R. China.
Porphyrins bearing the unique 18π electron tetrapyrrolic macrocycles exhibit interesting photophysical and photochemical properties and have been considered as promising ligands for the construction of functionalized metal-organic frameworks (MOFs). The combination of porphyrin-type ligands with lanthanide metals featured with diverse coordination environments to realize the novel functions as well as the diversity of the MOF is thus attractive but challenging. Herein, an unprecedented porphyrin-based samarium MOF (Sm-BCPP) composed of a 5,10-bis(4-carboxyphenyl)-10,20-diphenyl porphyrin (HBCPP) ligand and samarium-formed one-dimensional clusters has been constructed via a solvothermal approach, and the synthesized Sm-BCPP has excellent chemical stabilities, exhibiting red luminescence.
View Article and Find Full Text PDFAntibiotics (Basel)
December 2024
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow 117997, Russia.
Irumamycin (Iru) is a complex polyketide with pronounced antifungal activity produced by a type I polyketide (PKS) synthase. Iru features a unique hemiketal ring and an epoxide group, making its biosynthesis and the structural diversity of related compounds particularly intriguing. In this study, we performed a detailed analysis of the biosynthetic gene cluster (BGC) to uncover the mechanisms underlying Iru formation.
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