We investigated the ultrasonication-mediated effects on the Fmoc-based solid-phase peptide synthesis (SPPS). Our study culminated with the development of an ultrasound-assisted strategy (US-SPPS) that allowed for the synthesis of different biologically active peptides (up to 44-mer), with a remarkable savings of material and reaction time. Noteworthy, ultrasonic irradiation did not exacerbate the main side reactions and improved the synthesis of peptides endowed with "difficult sequences", placing the US-SPPS among the current high-efficient peptide synthetic strategies.
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http://dx.doi.org/10.1021/acs.orglett.9b02283 | DOI Listing |
J Nat Prod
January 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 PDFOrg Biomol Chem
January 2025
School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, 3010, Victoria, Australia.
Despite advances in solid phase peptide synthesis and peptide ligation, challenges remain in the assembly of polypeptides through coupling of peptide fragments. Herein we describe a new method for peptide fragment coupling employing the Ag(I)-promoted transformation of peptide thioamides. This process proceeds an isoimide-tethered intermediate, which undergoes an O-N acyl transfer to generate the polypeptide.
View Article and Find Full Text PDFDalton Trans
January 2025
Department of Chemistry, Università degli Studi di Milano, via C. Golgi 19, I-20133 Milan, Italy.
The synthesis of novel highly phosphorescent N^C^N tridentate platinum(II)-complex-peptide nucleic acid (PNA) bioconjugates was accomplished through the solid-phase approach. Melting temperature measurements and circular dichroism spectroscopy studies demonstrated that these conjugates maintain the PNA ability to recognize complementary ssDNA and ssRNA, though the length of the spacer between the metal center and the PNA sequence affects their hybridization properties. Noteworthy, the conjugation of PNA to this family of Pt(II) complexes significantly enhanced the luminescent features of the organometallic moiety, leading to increased quantum yields (82.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Engineering, Graduate School of Integrated Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
High-performance liquid chromatography (HPLC) plays a crucial role in purifying peptides and proteins and monitoring their reactions. Peptide hydrazides are widely employed intermediates in modern peptide/protein chemistry. However, they often exhibit peak tailing during HPLC purification and analysis.
View Article and Find Full Text PDFToxicon
January 2025
Applied Immunology and Morphology Research Centre, NuPMIA, Morphology Area, Faculty of Medicine, University of Brasília, UnB, Brasília, Distrito Federal, Brazil. Electronic address:
Amphibian skin is a rich source of molecules with biotechnological potential, including the tryptophyllin family of peptides. Here, we report the identification and characterization of two tryptophyllin peptides, FPPEWISR and FPWLLS-NH, from the skin of the Central Dwarf Frog, Physalaemus centralis. These peptides were identified through cDNA cloning and sequence comparison.
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