title: Revisiting oxytocin through the medium of isonitriles.
abstract: The reaction of thioamino acids and N-terminal peptides, mediated by hindered isonitriles and hydroxybenzotriazole, gives rise to peptide bonds. In one pathway, oxytocin was synthesized by eight such reiterative amidations. In another stereospecific track, oxytocin was constructed by native chemical ligation, wherein the two building blocks were assembled by thioacid amine amidation. The NMR spectra of oxytocin and dihydrooxytocin suggest a high level of preorganization in the latter, perhaps favoring oxidative folding.
authors: Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
authors: Ting
authors: T
authors: Wang
authors: Samuel J
authors: SJ
authors: Danishefsky
mesh_terms: D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010121:Oxytocin / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009570:Nitriles; D010121:Oxytocin