Bioorganic chemistry of cyclic ADP-ribose (cADPR).
The objective of this brief review is to present an overview of the bioorganic chemistry of cyclic-ADP-ribose (cADPR) with special emphasis on the methodology used for the synthesis of analogues of cADPR. New structural analogues of cADPR can be prepared using either the biomimetic method or ADP-ribosyl cyclase from Aplysia californica. For the most part, both procedures give similar product profiles, but higher yields are generally obtained with the enzymatic method. These synthetic methodologies have allowed the transformation of a variety of structurally modified analogues of NAD+ into their corresponding cyclic nucleotides. Several of these novel analogues are more potent than cADPR in inducing calcium release and are also more stable towards degradative enzymes. They could serve as valuable affinity probes for the isolation of cADPR-binding proteins.
School of Pharmacy, University of Wisconsin, Madison 53706, USA.
F J
FJ
Zhang
Q M
QM
Gu
C J
CJ
Sih
D036541:ADP-ribosyl Cyclase; D051997:ADP-ribosyl Cyclase 1; D000246:Adenosine Diphosphate Ribose / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry; D000255:Adenosine Triphosphate / Q000737:chemistry; D000345:Affinity Labels / Q000138:chemical synthesis; D000818:Animals; D015703:Antigens, CD; D000943:Antigens, Differentiation / Q000737:chemistry; D036563:Cyclic ADP-Ribose; D004795:Enzyme Stability; D006868:Hydrolysis; D007536:Isomerism; D008956:Models, Chemical; D009244:NAD+ Nucleosidase / Q000737:chemistry; D011487:Protein Conformation; D012617:Sea Urchins / Q000196:embryology
D000345:Affinity Labels; D015703:Antigens, CD; D000943:Antigens, Differentiation; D036563:Cyclic ADP-Ribose; D000246:Adenosine Diphosphate Ribose; D000255:Adenosine Triphosphate; D036541:ADP-ribosyl Cyclase; D009244:NAD+ Nucleosidase; D051997:ADP-ribosyl Cyclase 1