title: Straightforward synthesis of cyclic and bicyclic peptides.
abstract: Cyclic peptide architectures can be easily synthesized from cysteine-containing peptides with appending maleimides, free or protected, through an intramolecular Michael-type reaction. After peptide assembly, the peptide can cyclize either during the trifluoroacetic acid treatment, if the maleimide is not protected, or upon deprotection of the maleimide. The combination of free and protected maleimide moieties and two orthogonally protected cysteines gives access to structurally different bicyclic peptides with isolated or fused cycles.
authors.affiliation: Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.
authors.forename: Xavier
authors.initials: X
authors.lastname: Elduque
authors.forename: Enrique
authors.initials: E
authors.lastname: Pedroso
authors.forename: Anna
authors.initials: A
authors.lastname: Grandas
mesh_terms: D003500:Cyclization; D003545:Cysteine / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D008301:Maleimides; D010455:Peptides; D010456:Peptides, Cyclic; C043592:maleimide; D003545:Cysteine