title: Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides.
abstract: Among the available protocols, chemically driven approaches to oxidize cysteine may not be required for molecules that, under the native-like conditions, naturally fold in conformations ensuring an effective pairing of the right disulfide bridge pattern. In this contest, we successfully prepared the distinctin, a natural heterodimeric peptide, and some synthetic cyclic peptides that are inhibitors of the CXCR4 receptor. In the first case, the air oxidation reaction allowed to connect two peptide chains via disulfide bridge, while in the second case allowed the cyclization of rationally designed peptides by an intramolecular disulfide bridge. Computational approaches helped to either drive de-novo design or suggest structural modifications and optimal oxidization protocols for disulfide-containing molecules. They are able to both predict and to rationalize the propensity of molecules to spontaneously fold in suitable conformations to achieve the right disulfide bridges.
authors.affiliation: Institute of Biostructures and Bioimaging, National Research Council, 80138, Naples, Italy.
authors.forename: Enrica
authors.initials: E
authors.lastname: Calce
authors.forename: Rosa Maria
authors.initials: RM
authors.lastname: Vitale
authors.forename: Andrea
authors.initials: A
authors.lastname: Scaloni
authors.forename: Pietro
authors.initials: P
authors.lastname: Amodeo
authors.forename: Stefania
authors.initials: S
authors.lastname: De Luca
mesh_terms: D029845:Amphibian Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D023181:Antimicrobial Cationic Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D003500:Cyclization; D003545:Cysteine / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D017510:Protein Folding; D055503:Protein Multimerization
chemical_list: D029845:Amphibian Proteins; D023181:Antimicrobial Cationic Peptides; D004220:Disulfides; D010455:Peptides; D010456:Peptides, Cyclic; C531945:distinctin; D003545:Cysteine