Synthesis of peptides containing a sulfinamide or a sulfonamide transition-state isostere

Moree, W.J., van Gent, L.C., van der Marel, G.A. and Liskamp, R.M.J. (1993) Synthesis of peptides containing a sulfinamide or a sulfonamide transition-state isostere. Tetrahedron, 49(5), pp. 1133-1150. (doi: 10.1016/S0040-4020(01)86293-1)

Abstract

A versatile synthesis of peptides incorporating the sulfinamide or sulfonamide transition-state analogue is described. Apart from the easily accessible Gly-Xxx isosteres used as haptens to elicit catalytic antibodies, other amino acids than Gly can be prepared by α-alkylation of the sulfonamide containing peptides. This is illustrated with the synthesis of a potential HIV-protease inhibitor 27.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: Moree, W.J., van Gent, L.C., van der Marel, G.A., and Liskamp, R.M.J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• ISSN: 0040-4020