Revisiting oxytocin through the medium of isonitriles

T Wang, SJ Danishefsky

Index: Wang, Ting; Danishefsky, Samuel J. Journal of the American Chemical Society, 2012 , vol. 134, # 32 p. 13244 - 13247

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Citation Number: 10

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 ...