title: Supported oligomethionine sulfoxide and Ellman's reagent for cysteine bridges formation.
abstract: A large number of bioactive peptides are cyclized through a disulfide bridge. This structural feature is very important for both bioactivity and stability. The oxidation of cysteine side chains is challenging not only to avoid intermolecular reaction leading to oligomers and oxidation of other residues but also to remove solvents and oxidant such as dimethyl sulfoxide. Supported reagents advantageously simplify the work-up of such disulfide bond formation, but may lead to a significant decrease in yield of the oxidized product. In this study, two resins working through different mechanisms were evaluated: Clear-Ox, a supported version of Ellman's reagent and Oxyfold, consisting in a series of oxidized methionine residues. The choice of the supported reagent is discussed on the light of reaction speed, side-products formation and yield considerations.
authors.affiliation: Genepep SA, Les Coteaux Saint Roch, 12 Rue du Fer à Cheval, 34430 St Jean de Védas, France.
authors.forename: Luisa
authors.initials: L
authors.lastname: Ronga
authors.forename: Pascal
authors.initials: P
authors.lastname: Verdié
authors.forename: Pierre
authors.initials: P
authors.lastname: Sanchez
authors.forename: Christine
authors.initials: C
authors.lastname: Enjabal
authors.forename: Amélie
authors.initials: A
authors.lastname: Maurras
authors.forename: Magalie
authors.initials: M
authors.lastname: Jullian
authors.forename: Karine
authors.initials: K
authors.lastname: Puget
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
authors.forename: Gilles
authors.initials: G
authors.lastname: Subra
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry; D004228:Dithionitrobenzoic Acid / Q000737:chemistry*; D008715:Methionine / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D004220:Disulfides; D016877:Oxidants; D004228:Dithionitrobenzoic Acid; D008715:Methionine; D003545:Cysteine; D012451:Safrole; C005746:sulfoxide; D004121:Dimethyl Sulfoxide