α-Sulfonpeptide

α-Sulfonopeptides:

Backbone modified peptides in which at least one of the aminoacids is replaced by one or more α-aminosulfonic acids are called α-sulfonopeptides. Due to the tetrahedral geometry around the sulphur atom those peptidomimetics resemble the intermediate for the peptide bond hydrolysis and therefore they are also called transition state isosteres^[1]. Thus α-sulfonopeptides might be, just like the more intensively studied β-sulfonopeptides^[2] and vinylogous sulfonopeptides^[3], candidates for protease inhibitors with potential therapeutic application. However, the synthesis of α-sulfonopeptides has remained, except for an approach by Curtius Rearrangement^[4], elusive due to the susceptibility of α-aminosulfonic acids to decomposition during the activation of the sulfonic acid group^[4],[5]. In order to circumvent the activation of the sulfonic acid group we are investigating, among other methods, the electrophilic amination of N-protected α-amino sulfinates^[5],[6],as reported by Mulliez et al., further.

[6] M. Mulliez, WO 98/04522 A1, 1998