Total Synthesis and Pharmacological Investigation of Cordyheptapeptide A.

Molecules

Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad & Tobago, West Indies.

Published: May 2017

The present investigation reports the synthesis of a phenylalanine-rich -methylated cyclopeptide, cordyheptapeptide A (), previously isolated from the insect pathogenic fungus sp. BCC 1788, accomplished through the coupling of -methylated tetrapeptide and tripeptide fragments followed by cyclization of the linear heptapeptide unit. Structure elucidation of the newly synthesized cyclopolypeptide was performed by means of FT-IR, ¹H-NMR, C-NMR, and fast atom bombardment mass spectrometry (FABMS), and screened for its antibacterial, antidermatophytic, and cytotoxic potential. According to the antimicrobial activity results, the newly synthesized -Methylated cyclopeptide exhibited potent antibacterial activity against Gram-negative bacteria and and antifungal activity against dermatophytes and at a concentration of 6 μg/mL, in comparison to the reference drugs, gatifloxacin and griseofulvin. In addition, cyclopolypeptide displayed suitable levels of cytotoxicity against (DLA) and (EAC) cell lines.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152760PMC
http://dx.doi.org/10.3390/molecules22060682DOI Listing

Publication Analysis

Top Keywords

-methylated cyclopeptide
8
newly synthesized
8
total synthesis
4
synthesis pharmacological
4
pharmacological investigation
4
investigation cordyheptapeptide
4
cordyheptapeptide investigation
4
investigation reports
4
reports synthesis
4
synthesis phenylalanine-rich
4

Similar Publications

Pheophytin-a derivatives possessing plastoquinone and phylloquinone analogs in the peripheral 3-substituent were prepared by Friedel-Crafts reactions of a 3-hydroxymethyl-chlorin as one of the chlorophyll-a derivatives with benzo- and naphthohydroquinones, respectively, and successive oxidation of the 1,4-dihydroxy-aryl groups in the resulting dehydration products. The 3-quinonylmethyl-chlorins exhibited ultraviolet-visible absorption and circular dichroism spectra in acetonitrile, which were composed of those of the starting 3-hydroxymethyl-chlorin and the corresponding methylated benzo- and naphthoquinones. No intramolecular interaction between the chlorin and quinone π-systems was observed in the solution owing to the methylene spacer.

View Article and Find Full Text PDF

Micromycetes from the genus Alternaria are commonly found in plant food raw materials, and their produced emerging mycotoxins (EMT) pose a risk to human health. Based on polyphase taxonomy, we studied the species composition of the Alternaria spp. population in samples of Russian grain and berries; non-toxinogenic species of Alternaria of the Infectoriae section and toxinogenic species of the Alternaria section were found.

View Article and Find Full Text PDF

Sulfonium is an electrophilic and biocompatible group that is widely applied in synthetic chemistry on small molecules. However, there have been few developments of peptide or protein-based sulfonium tools. We recently reported sulfonium-mediated tryptophan crosslinking and developed NleSme2 (norleucine-dimethylsulfonium) peptides as dimethyllysine mimics that crosslink site-specific methyllysine readers.

View Article and Find Full Text PDF

Three New Depsipeptides, Homiamides A-C, Isolated from sp., ROA-065.

Molecules

November 2024

Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea.

Three new depsipeptides, homiamides A-C (-), were isolated from a marine sediment-derived strain of sp., ROA-065. The planar structures of homiamides A-C (-) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data.

View Article and Find Full Text PDF

The rufomycins are a family of nonribosomal cyclic peptides isolated from the deep sea-dwelling Herein, we describe the total synthesis of six congeners in the rufomycin family. Synthesis was achieved through a modular solid-phase strategy, incorporating synthetic nonproteinogenic amino acids: l-2-amino-4-hexenoic acid, prenyl-l-tryptophan (and related ()-epoxide), and -methyl-δ-hydroxy-l-leucine. Following macrolactamization, these peptides were further diversified through late-stage oxidation and secondary cyclization to furnish a library of six synthetic natural products.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!