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

Article abstract of DOI:10.1016/S0040-4020(01)86293-1

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.