Synthesis of N-ε-(indole-3-acetyl)-l-lysine

Add time:09/04/2019    Source:sciencedirect.com

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-nitrophenylester. 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.

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