New Mild and Efficient Synthesis of Peptidosulfonamides

Abstract

This article describes a new route to peptidosulfonamide. Our study shows how sulfinamides were first obtained via nucleophilic cleavage of 3,6‐dihydrothiazine‐1‐oxide system and how the products can be subjected to oxidation with m‐chloroperbenzoic acid to give sulfonamides in good yield.

Keywords:

• 3,6‐dihydrothiazine‐1‐oxide system
• m‐chloroperbenzoic acid
• peptidomimetics
• peptidosulfonamide
• tripeptide

Acknowledgments

The authors thank Laura Salvini (Centro di Analisi e Determinazioni Strutturali, University of Siena) for recording ESI‐MS spectra. This work was financially supported by the University of Siena (Piano di Ateneo per la Ricerce (PAR) Project 2006) and by Ministero Istruzione, Università e Ricerca (MIUR) (Piano di Ricerca di Interesse Nazionale (PRIN) project.

Notes

*Double signals due to the presence of diastereoisomers.