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A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

✍ Scribed by Ravi S. Lamani; G. Nagendra; Vommina V. Sureshbabu

Book ID: 104098042
Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 713 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.07.004

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✦ Synopsis

Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained.

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