SYNTHESIS OF N-&ε-(INDOLE-3-ACETYL)-L-LYSINE

Article abstract of DOI:10.1016/0031-9422(93)85388-8

N-ε-(indole-3-acetyl)-L-Lysine (ε-IAA-Lys) and its N-α-acetyl derivative (Ac-ε-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-α-CBz-L-lysine p-nitrophenyl ester.The same synthetic strategy was used to obtain the unnatural conjugate, N-α-(indole-3-acetyl)-L-lysine (α-IAA-Lys) and its N-ε-acetyl derivative (Ac-α-IAA-Lys).Comparative bioassay for auxin activity on wheat coleoptiles proved that ε-IAA-Lys and Ac-ε-IAA-Lys significantly stimulated their growth, although their activity was considerably less than IAA.No activity was shown by α-IAA-Lys and Ac-α-IAA-Lys. Key words: Pseudomonas syringae subsp. savastanoi; olive and oleander knot disease; auxins; synthesis; N-ε-(indole-3-acetyl)-L-lysine and its N-α-acetyl derivative; N-α-(indole-3-acetyl)-L-lysine and its N-ε-acetyl derivative.