Recent advances on cyclodepsipeptides: biologically active compounds for drug research

Frontiers in Microbiology, Journal Year: 2023, Volume and Issue: 14

Published: Oct. 2, 2023

Cyclodepsipeptides are a large family of peptide-related natural products consisting hydroxy and amino acids linked by amide ester bonds. A number cyclodepsipeptides have been isolated characterized from fungi bacteria. Most them showed antitumor, antifungal, antiviral, antimalarial, antitrypanosomal properties. Herein, this review summarizes the recent literatures (2010-2022) on progress bacteria except for those marine origin, in order to enrich our knowledge about their structural features biological sources.

Language: Английский

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Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Marine Drugs, Journal Year: 2023, Volume and Issue: 21(10), P. 547 - 547

Published: Oct. 22, 2023

In the post-antibiotic era, rapid development of antibiotic resistance and shortage available antibiotics are triggering a new health-care crisis. The discovery novel potent to extend pipeline is urgent. Small-molecule antimicrobial peptides have wide variety spectra multiple innovative mechanisms due their rich structural diversity. Consequently, they become research hotspot considered be promising candidates for next-generation antibiotics. Therefore, we compiled collection small-molecule derived from marine microorganisms last fifteen years show recent advances in this field. We categorize these compounds into three classes—cyclic oligopeptides, cyclic depsipeptides, lipopeptides—according features, present sources, structures, spectrums, with discussion structure activity relationships action some compounds.

Language: Английский

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Catalytic Cleavage of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group under Neat Conditions

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3284 - 3288

Published: March 28, 2024

This work reports the first solvent-free catalytic approach for cleavage of fluorenylmethoxycarbonyl (Fmoc) protecting group from amine and alcohol functionalities. Various saccharide, peptide, glyco-amino acid substrates were efficiently deprotected by simple treatment with 20 mol % neat 4-dimethylaminopyridine (DMAP) (one effective base catalysts found), without any solvent or stoichiometric additives. Small model structures finally assembled through one-pot, base-catalyzed, multistep sequences combining Fmoc esterification, amidation, and/or glycosylation steps.

Language: Английский

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Secondary metabolites from cyanobacteria: source, chemistry, bioactivities, biosynthesis and total synthesis

Phytochemistry Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: April 22, 2024

Language: Английский

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Modular, Scalable Total Synthesis of Lapparbin with a Noncanonical Biaryl Linkage

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 15, 2024

Abstract We report the development of a novel synthetic approach for highly strained atrop‐Tyr C‐6‐to‐Trp N‐1′ linkage, which can be executed on decagram scale using modular strategy involving palladium‐catalyzed C−H arylation followed by Larock macrocyclization. The first total synthesis lapparbin ( 1 ) was achieved applying this strategy. Furthermore, utilizing and macrocyclization, discovered in ), demonstrated to applicable various arbitrary biaryl linkages, including non‐natural types.

Language: Английский

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Modular, Scalable Total Synthesis of Neopetromin^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3023 - 3028

Published: Aug. 21, 2024

Comprehensive Summary The first total synthesis of neopetromin, featuring the highly strained Tyr C‐6‐to‐Trp N‐1’ linkage, is hereby reported. This modular synthetic strategy, employing C—H arylation and Larock macrocyclization, offers a novel approach to various RiPPs natural product families.

Language: Английский

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The Epiphyte Bacillus sp. G2112 Produces a Large Diversity of Nobilamide Peptides that Promote Biofilm Formation in Pseudomonads and Mycobacterium aurum

Biomolecules, Journal Year: 2024, Volume and Issue: 14(10), P. 1244 - 1244

Published: Oct. 1, 2024

sp. G2112, an isolate from cucumber plants that inhibited plant pathogens, produces not only surfactins, iturins, and fengycins common to many

Language: Английский

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Marine Peptides: Potential Basic Structures for the Development of Hybrid Compounds as Multitarget Therapeutics for the Treatment of Multifactorial Diseases

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(23), P. 12601 - 12601

Published: Nov. 23, 2024

Marine-derived peptides display potent antihypertensive, antioxidant, analgesic and antimicrobial biological effects. Some of them have also been found to anticancer activity via various mechanisms differing from those continental organisms. This diversity properties-together with the peptides' efficacy, which has confirmed in several vitro vivo studies-make these compounds attractive as functional ingredients pharmacy, especially regard multitarget drugs known hybrids. Given possibilities offered by chimeric structures, it is expected that a hybridization strategy based on marine-derived compound could result long-awaited success development new effective combat range complex diseases. However, despite fact such hybrids may exceed their parent compounds, there still an urgent need carefully determine potential off-targets thus possible clinically important side above, aim this paper provide information marine origin peptide structures verify occurrence usage hybrid built structures. Furthermore, authors believe presented here will serve increase public awareness opportunities arising combination strategies molecules properties, thereby accelerating drug candidates.

Language: Английский

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Modular, Scalable Total Synthesis of Lapparbin with a Noncanonical Biaryl Linkage

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(42)

Published: July 15, 2024

Abstract We report the development of a novel synthetic approach for highly strained atrop‐Tyr C‐6‐to‐Trp N‐1′ linkage, which can be executed on decagram scale using modular strategy involving palladium‐catalyzed C−H arylation followed by Larock macrocyclization. The first total synthesis lapparbin ( 1 ) was achieved applying this strategy. Furthermore, utilizing and macrocyclization, discovered in ), demonstrated to applicable various arbitrary biaryl linkages, including non‐natural types.

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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