ON THE "NORMALIZING FACTOR" FOR THE TOMATO MUTANT CHLORONERVA-XIV. SYNTHESIS OF THE PROLINE ANALOGUE OF THE PHYTOSIDEROPHORE NICOTIANAMINE

Article abstract of DOI:10.1016/S0040-4020(01)88567-7

The synthesis of (2S:3'S:3"S)-N-<3-(3-amino-3-carboxypropylamino)-3-carboxypropyl>-proline (1), a nicotianamine analogue with a 5-membered ring, was achieved by stepwise combination of S-proline ethyl ester (3) and (3S)-3-ethoxycarbonyl-3-trifluoroacetylaminopropionaldehyde (4) via reductive coupling.Compound 1 exhibits a smaller biological effect than nicotianamine (2) on phenotypical normalization of the tomato mutant chloronerva.