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Stylissamide B was successfully synthesized for the first time using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) followed by cyclization in solution phase. The Fmoc-SPPS process was monitored using the reversible detection method for amino groups (ReD-A method). The linear peptide, Pro-Pro-Ile-Tyr-Pro-Phe-Pro, was cyclized to form stylissamide B. The spectral data obtained were in agreement with previously reported literature, thereby confirming the reliability of the synthetic method.
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http://dx.doi.org/10.1002/psc.70028 | DOI Listing |
J Pept Sci
June 2025
Department of Chemistry and Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata, Japan.
Stylissamide B was successfully synthesized for the first time using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) followed by cyclization in solution phase. The Fmoc-SPPS process was monitored using the reversible detection method for amino groups (ReD-A method). The linear peptide, Pro-Pro-Ile-Tyr-Pro-Phe-Pro, was cyclized to form stylissamide B.
View Article and Find Full Text PDFJ Nat Prod
February 2025
Department of Chemistry and Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan.
We investigated the chemical structures and conformational isomers of the cyclic heptapeptides stylissamide H and euryjanicin A isolated from marine sources. Despite sharing the same molecular structure, stylissamide H and euryjanicin A exhibit different conformational isomers in solution and solid states. The main difference arises from the configurations of the two Pro residues.
View Article and Find Full Text PDFMar Drugs
August 2020
Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, Italy.
Feature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, , known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic peptides in the sponge that had never been detected in previous work and appeared to be new compounds. The most abundant one was isolated and shown to be a new proline-rich cyclic heptapetide that was called stylissamide L ().
View Article and Find Full Text PDFMar Drugs
May 2020
Department of Pharmacognosy, Faculty of Pharmacy, Deraya University, New Minia 61111, Egypt.
Bioactivity-guided isolation supported by LC-HRESIMS metabolic profiling led to the isolation of two new compounds, a ceramide, stylissamide A (), and a cerebroside, stylissoside A (), from the methanol extract of the Red Sea sponge . Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. The bioactive extract's metabolomic profiling showed the existence of various secondary metabolites, mainly oleanane-type saponins, phenolic diterpenes, and lupane triterpenes.
View Article and Find Full Text PDFMar Drugs
December 2016
Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad and Tobago.
A natural heptacyclopeptide, stylissamide G (), previously isolated from the Bahamian marine sponge from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, ¹H NMR, C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential against , and at 2 mg/mL and in addition, potent antifungal activity against pathogenic and dermatophytes and at a concentration of 6 μg/mL.
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