Tetrahedron

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

…, LC van Gent, GA van der Marel, RMJ Liskamp

Index: Moree, Wilna J.; Van Gent, Liesbeth C.; Van Der Marel, Gijs A.; Liskamp, Rob M. J. Tetrahedron, 1993 , vol. 49, # 5 p. 1133 - 1150

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Citation Number: 67

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.