Isolation, Total Synthesis and Structure Determination of Antifungal Macrocyclic Depsipeptide, Tetraselide

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Macrocyclic peptides, including depsipeptides, are an emerging new modality in drug discovery research. Tetraselide, antifungal cyclic peptide isolated from a marine-derived filamentous fungus, possesses unique amphiphilic structural feature consisting of five consecutive β-hydroxy-amino acid residues and fatty moieties. Because the structure elucidation naturally occurring product left six stereocenters ambiguous, we implemented bioinformatic analyses, chemical degradation studies chiral pool fragment synthesis to identify two undetermined stereocenters. Convergent total four remaining plausible isomers tetraselide was accomplished via liquid-phase (LPPS) using soluble hydrophobic tag auxiliaries. The key advances involve coupling by serine/threonine ligation (STL) reaction head-to-tail macrolactamization carrier-supported precursors that enabled systematic elaboration peptides. Ultimately, determined absolute this natural product.

Language: Английский

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Isolation, Total Synthesis and the Structure Determination of the Antifungal Macrocyclic Depsipeptide, Tetraselide

Published: May 31, 2024

Macrocyclic peptides and depsipeptides are the emerging class of a new modality in drug discovery research. Tetraselide, an antifungal cyclic peptide isolated from marine-derived filamentous fungus, possesses unique amphiphilic structural feature that represents five consecutive β-hydroxy-amino acid fatty moieties. Because structure elucidation naturally occurring product left six stereocenters ambiguous, we implemented bioinformatic analyses, chemical degradation study chiral pool fragment synthesis to identify two undetermined stereochemistry. Convergent total four remaining plausible isomers tetraselide was accomplished via liquid-phase using soluble hydrophobic tag auxiliaries. The key advance involves coupling by serine/threonine ligation reaction head-to-tail macrolactamization carrier-supported precursors enabled systematic elaboration peptides. Ultimately, determined absolute this natural product.

Language: Английский

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Isolation, Total Synthesis and the Structure Determination of the Antifungal Macrocyclic Depsipeptide, Tetraselide

Published: June 14, 2024

Macrocyclic peptides and depsipeptides are the emerging class of a new modality in drug discovery research. Tetraselide, an antifungal cyclic peptide isolated from marine-derived filamentous fungus, possesses unique amphiphilic structural feature that represents five consecutive β-hydroxy-amino acid fatty moieties. Because structure elucidation naturally occurring product left six stereocenters ambiguous, we implemented bioinformatic analyses, chemical degradation study chiral pool fragment synthesis to identify two undetermined stereochemistry. Convergent total four remaining plausible isomers tetraselide was accomplished via liquid-phase using soluble hydrophobic tag auxiliaries. The key advance involves coupling by serine/threonine ligation reaction head-to-tail macrolactamization carrier-supported precursors enabled systematic elaboration peptides. Ultimately, determined absolute this natural product.

Language: Английский

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Origin and characterization of cyclodepsipeptides: Comprehensive structural approaches with focus on mass spectrometry analysis of alkali‐cationized molecular species

Mass Spectrometry Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 21, 2024

Abstract Cyclodepsipeptides (CDPs) represent a huge family of chemically and structurally diverse molecules with wide ability for molecular interactions. CDPs are cyclic peptide‐related natural products made up both proteinogenic nonproteinogenic amino acids linked by amide ester bonds. The combined use different analytical methods is required to accurately determine their integral structures including stereochemistry, thus allowing deeper insights into often‐intriguing bioactivities possible usefulness. Our goal present the various developed characterize CDPs. Presently, Marfey's method NMR (nuclear magnetic resonance) still considered best characterizing CDP configuration. Nevertheless, electrospray‐high resolution tandem mass spectrometry (ESI‐HRMS/MS) great value efficiently resolving CDP's composition sequences. For instance, recent data shows that fragmentation cationized (e.g., [M + Li] Na] ) leads selective cleavage bonds specific product ions ( b series) useful get unprecedented sequence information. Thus, after brief presentation structure, biological functions, biosynthesis, we also provide historic overview these approaches as well advantages limitations special emphasis on emergence based HRMS/MS through fundamental works applications.

Language: Английский

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Total Synthesis of Marformycins A and D

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 10056 - 10060

Published: Nov. 12, 2024

We report the synthesis of antimicrobial cyclodepsipeptides marformycin A (

Language: Английский

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