Oxidation of a thioether linkage in thioether-closed macrocyclic peptides led to collision-induced site-selective linearization of the peptides. This method has allowed for sequencing of thioether macrocyclic peptides. The utility of the sequencing method was demonstrated by identifying the correct peptide sequences from a virtually randomized thioether macrocyclic peptide library.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d4cc03179b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Water-soluble platinum and palladium porphyrins with peripheral ethyl phosphonic acid substituents: synthesis, aggregation in solution, and photocatalytic properties.
Dalton Trans
January 2025
Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB), UMR 6302 CNRS, Université de Bourgogne, 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, France.
Water-soluble porphyrins have garnered significant attention due to their broad range of applications in biomedicine, catalysis, and material chemistry. In this work, water-soluble platinum(II) and palladium(II) complexes with porphyrins bearing ethyl phosphonate substituents, namely, Pt/Pd 10-(ethoxyhydroxyphosphoryl)-5,15-di(-carboxyphenyl)porphyrins (M3m, M = Pt(II), Pd(II)) and Pt/Pd 5,10-bis(ethoxyhydroxyphosphoryl)-10,20-diarylporphyrins (M1d-M3d; aryl = -tolyl (1), mesityl (2), -carboxyphenyl (3)), were synthesized by alkaline hydrolysis of the corresponding diethyl phosphonates M6m and M4d-M6d. NMR, UV-vis, and fluorescence spectroscopy revealed that the mono-phosphonates M3m tend to form aggregates in aqueous media, while the bis-phosphonates M3d exist predominantly as monomeric species across a wide range of concentrations (10-10 M), ionic strengths (0-0.
View Article and Find Full Text PDFKinetic Analysis of Cyclization by the Substrate-Tolerant Lanthipeptide Synthetase ProcM.
ACS Catal
December 2024
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
Lanthipeptides are ribosomally synthesized and post-translationally modified peptides (RiPPs) characterized by the presence of thioether cross-links called lanthionine and methyllanthionine, formed by dehydration of Ser/Thr residues and Michael-type addition of Cys side chains onto the resulting dehydroamino acids. Class II lanthipeptide synthetases are bifunctional enzymes responsible for both steps, thus generating macrocyclic natural products. ProcM is part of a group of class II lanthipeptide synthetases that are known for their remarkable substrate tolerance, having large numbers of natural substrates with highly diverse peptide sequences.
View Article and Find Full Text PDFCell-Permeable Peptide Inhibitors of the p53-hDM2 Interaction via Foldamer Helix Mimicry and Bis-Thioether Stapling.
J Med Chem
January 2025
Univ. Bordeaux, CNRS, Bordeaux INP, CBMN, UMR 5248, IECB, F-33607 Pessac, France.
Combining helical foldamers with α-peptides can produce α-helix mimetics with a reduced peptide character and enhanced resistance to proteolysis. Previously, we engineered a hybrid peptide-oligourea sequence replicating the N-terminal α-helical domain of p53 to achieve high affinity binding to hDM2. Here, we further advance this strategy by combining the foldamer approach with side chain cross-linking to create more constrained cell-permeable inhibitors capable of effectively engaging the target within cells.
View Article and Find Full Text PDFBiosynthesis of Antimicrobial Ornithine-Containing Lacticin 481 Analogues by Use of a Combinatorial Biosynthetic Pathway in .
ACS Synth Biol
December 2024
Department of Molecular Genetics, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Groningen 9747 AG, The Netherlands.
Lacticin 481, a ribosomally synthesized and post-translationally modified peptide (RiPP), exhibits antimicrobial activity, for which its characteristic lanthionine and methyllanthionine ring structures are essential. The post-translational introduction of (methyl)lanthionines in lacticin 481 is catalyzed by the enzyme LctM. In addition to macrocycle formation, various other post-translational modifications can enhance and modulate the chemical and functional diversity of antimicrobial peptides.
View Article and Find Full Text PDFCucurbit[8]uril-stabilized charge transfer: An efficient supramolecular approach toward a heterogeneous organic photocatalyst for aerobic oxidation reactions.
Chemistry
December 2024
Hunan Normal University, Department of Chemistry, Hunan Normal University, 410081, Changsha, CHINA.
Host-stabilized charge transfer (HSCT) has been widely utilized in macrocycle-derived supramolecular assemblies and architectures. However, there has been less research attention focused on the direct fabrication of pure organic photocatalysts using HSCT. Herein, four viologen derivatives (m-PV2+, m-BPV2+, d-PV2+, and d-BPV2+) with different electron donor-acceptor (D-A) structures were synthesized.
View Article and Find Full Text PDFWant 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!