Abstract
Abstract N-(O,O-diisopropyl)phosphoryl-arginine (DIPP—Arg) 3 and N-(0,0-diisopropyl)phosphoryl-arginine methyl ester (DIPP—Arg—OMe) 4a were synthesized. In compound 3 the co-participation of the three functional groups of the phosphoryl, guanidine and carboxyl was essential for the ester exchange reaction at the phosphoryl group and esterification at carboxyl group. In contrast, when the carboxyl group was blocked, as in compound 4a, no corresponding reaction occurred. A mixed anhydride penta-coordinate phosphorus transition state was proposed for the self-activation mechanism.
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