title: One-pot peptide ligation-desulfurization at glutamate.
abstract: An efficient methodology for ligation at glutamate (Glu) is described. A γ-thiol-Glu building block was accessed in only three steps from protected glutamic acid and could be incorporated at the N-terminus of peptides. The application of these peptides in one-pot ligation-desulfurization chemistry is demonstrated with a range of peptide thioesters, and the utility of this methodology is highlighted through the synthesis of the osteoporosis peptide drug teriparatide (Forteo).
authors.affiliation: School of Chemistry, The University of Sydney , NSW 2006, Australia.
authors.forename: Katie M
authors.initials: KM
authors.lastname: Cergol
authors.forename: Robert E
authors.initials: RE
authors.lastname: Thompson
authors.forename: Lara R
authors.initials: LR
authors.lastname: Malins
authors.forename: Peter
authors.initials: P
authors.lastname: Turner
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Payne
mesh_terms: D018698:Glutamic Acid / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D019379:Teriparatide / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010455:Peptides; D019379:Teriparatide; D018698:Glutamic Acid