Abstract
This chapter describes the preparation of cyclic ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide phosphate (NAADP) caged as 1-(2-nitrophenyl)ethyl (NPE) phosphoesters, and characterization of their photolysis. The cyclic structure of cADPR is formed by linking the N-1 nitrogen of the adenine ring in NAD + to the terminal ribose, displacing the nicotinamide group. This cyclization can be performed by treatment of NAD + with the ubiquitous enzyme ADP-ribosyl cyclase or by heating solutions of NAD + with sodium bromide in dimethyl sulfoxide (DMSO). Nicotinic acid adenine dinucleotide phosphate is formed by replacing the nicotinamide group of NADP with nicotinic acid. This can be accomplished by treatment of NADP with an aqueous base or by ADP-ribosyl cyclasecatalyzed exchange of the nicotinamide in NADP with nicotinic acid. The use of photolabile, or “caged,” precursors of cADPR and NAADP makes it possible to generate these signaling molecules with precise spatial and temporal resolution by UV photolysis when and where desired.
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