Chiral N-(Coumarin-3-ylcarbonyl)-α-amino acids: Fluorescent markers for amino acids and dipeptides

Abstract

N-(Coumarin-3-ylcarbonyl)benzotriazole has been coupled with free amino acids, N-terminal-protected lysines and dipeptides to afford fluorescent amino acids and dipeptides (76-89% yield) with retention of original chirality. N α- and Nε-Coumarin-labeled lysines are obtained by simple, two-step procedures. Nα-Cbz-Nε- (Coumarin-3-ylcarbonyl)-L-lysine is demonstrated to be an optically active fluorescent marker for labeling amino acids in solution-phase syntheses. © Thieme Stuttgart.