Chemical synthesis of the novel Ca2+ messenger NAADP.
The first total chemical synthesis of nicotinamide adenine dinucleotide phosphate (beta-NADP, 2) as a single isomer was achieved. This was subsequently converted into the important second messenger nicotinic acid adenine dinucleotide phosphate (p-NAADP) 1 and the identity of this material confirmed by biological evaluation. This flexible synthetic route offers new opportunities for the generation of NAADP 1 analogues that cannot be generated directly from NADP 2 or mainly enzymatic methods.
Dowden
James
J
Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath BA2 7AY, UK.
Brown
Richard S
RS
Moreau
Christelle
C
Galione
Antony
A
Potter
Barry V L
BV
D000818:Animals; D001048:Aplysia; D002118:Calcium / Q000378:metabolism*; D020013:Calcium Signaling; D002626:Chemistry, Pharmaceutical / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009249:NADP / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015290:Second Messenger Systems; D013696:Temperature
D009249:NADP; C024376:NAADP; D002118:Calcium