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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.

SUBMITTER: Wang T

PROVIDER: S-EPMC3433685 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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Revisiting oxytocin through the medium of isonitriles.

Wang Ting T Danishefsky Samuel J SJ

Journal of the American Chemical Society 20120802 32

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 fa ...[more]

PMID: 22830449

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