SYNTHESIS OF N-EPSILON-(INDOLE-3-ACETYL)-L-LYSINE

N-epsilon-(indole-3-acetyl)-L-Lysine (epsilon-IAA-Lys) and its N-alpha-acetyl derivative (Ac-epsilon-IAA-Lys), products of the metabolism of indole-3-acetic acid (IAA) in Pseudomonas syringae subsp. savastanoi, have been synthesized by a conjugation of IAA with the N-alpha-CBZ-L-lysine p-nitrophenylester. The same synthetic strategy was used to obtain the unnatural conjugate, N-alpha-(indole-3-acetyl)-L-lysine (alpha-IAA-Lys) and its N-epsilon-acetyl derivative (Ac-alpha-IAA-Lys). Comparative bioassay for auxin activity on wheat coleoptiles proved that epsilon-IAA-Lys and Ac-epsilon-IAA-Lys significantly stimulated their growth, although their activity was considerably less than IAA. No activity was shown by alpha-IAA-Lys and Ac-alpha-IAA-Lys