title: Synthesis of all-L cyclic tetrapeptides using pseudoprolines as removable turn inducers.
abstract: Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.
authors.affiliation: School of Chemistry, The University of Sydney, 2006 NSW, Australia.
authors.forename: Kelly A
authors.initials: KA
authors.lastname: Fairweather
authors.forename: Nima
authors.initials: N
authors.lastname: Sayyadi
authors.forename: Ian J
authors.initials: IJ
authors.lastname: Luck
authors.forename: Jack K
authors.initials: JK
authors.lastname: Clegg
authors.forename: Katrina A
authors.initials: KA
authors.lastname: Jolliffe
mesh_terms: D008958:Models, Molecular; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D009842:Oligopeptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C505976:pseudoproline; D011392:Proline