Diketopinic acid-a novel reagent for the modification of arginine§.

ABSTRACT

Diketopinic acid has been synthesized and shown to be a reagent of choice for specific, reversible modification of the guanidine groups of arginine residues. Diketopinic acid is a yellow crystalline substance and the carboxyl group of the reagent is a convenient handle for attachment to other molecules. The adducts of diketopinoyl derivatives with the guanidine group are cleaved by 0·2 M o-phenylenediamine at pH 8–9. The modification and regeneration of arginine and of arginyl residues in soyabean trypsin inhibitor and insulin are presented as demonstrations of the use of the reagent. The use of diketopinoyl resin in the separation of oxidized A and B chains of insulin has been discussed.