A Selective Photoaffinity Ligand for the Kainate Class of Excitatory Amino Acid Receptor

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Abstract
The isopropenyl side chain of kainic acid (KA) has been replaced with a trifluoromethyldiazoketone group, resulting in a derivative ("diazoKA") that gives efficient photo-induced crosslinking to the active site of the KA class of glutamate receptor. The incorporation of this functional group is accomplished via a simple, one step coupling of a carboxylic acid and 2,2,2-trifluorodiazoethane in a procedure that should be generally applicable to the preparation of other photoaffinity labels. Major advantages include excellent stability towards acidic conditions, even Boc and t-butyl ester deprotection, as well as a reduced tendency to undergo (non-productive) Wolff rearrangement after binding and irradiation. The observed crosslinking paves the way for identifying the active site residues of the KA receptor.

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