Site-selective incorporation of thioamide-linkages into a growing peptide

Article abstract of DOI:10.1016/S0040-4020(99)00234-3

The use of endothiodipeptide anilides, which were obtained in high yields by a variation of the 'azirine/oxazolone method', for the synthesis of longer endothiopeptides is described. With this novel methodology, epimerically pure endothiopeptides with the thiocarbonyl group next to the bulky Aib were prepared in satisfactory yields. The structures of two endothiotripeptides and one endothiotetrapeptide were established by single- crystal X-ray crystallography.