Synthesis of 6-azido-1-oxo-indan-4-oyl isoleucine; a photoaffinity approach to plant signaling

Article abstract of DOI:10.1016/S0040-4020(99)00097-6

The synthesis of the photoreactive 6-azido-1-oxo-indanoyl isoleucine (3), as a molecular probe for the identification of putative receptors and binding proteins involved in stress signaling of plants, is described. The biological activity of the photolabile azide 3 comes close to that of the bacterial phytotoxin coronatine (1). Photodecomposition of 3 in the presence of myoglobin is assumed to proceed via an didehydroazepine intermediate and results in significant binding of the probe to the model protein.