Position | Suitable Analog | Effects |
Purine N1 |
Donor/acceptor potential changed |
|
Purine C2 |
No hydrogen bonding |
|
Purine N3 |
3-deaza cGMP (inquire) |
N3 electron pair lacking |
Purine O6 |
No hydrogen bonding via oxo group |
|
Purine N7 |
N7 electron pair lacking |
|
Purine C8 |
Syn/anti equilibrium, steric effects |
|
Ribose 2'- O |
No hydrogen bonding at 2'-OH, no hydrogen bond donor |
|
Ribose 3'- O |
3'-NH-cGMP (inquire) |
H-bridge donor/acceptor potential changed |
Ribose 5'- O |
5'-NH-cGMP (inquire) |
H-bridge donor/acceptor potential changed |
Phosphate ORp |
Sulfur/oxygen exchange (exocyclic equatorial position at phosphorus) |
|
Phosphate OSp |
Sulfur/oxygen exchange (exocyclic axial position at phosphorus) |
|
Phosphate O- |
No negative charge at phosphorus |
Selected References:
For an extended list of articles on mapping of cyclic nucleotide-responsive receptors, please refer to B. Jastorff, University of Bremen, publication list.
1 |
Corbin, J.D.; Øgreid, D.; Miller, J.; Suva, R.H.; Jastorff, B.; Døskeland, S.O., J. Biol. Chem., 261, 1208 - 1214 (1986): "Studies of cGMP Analog Specificity and Function of the Two Intrasubunit Binding Sites of cGMP-dependent Protein Kinase" |
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2 |
Wolfe, L.; Corbin, J.D.; Francis, S.H., J. Biol. Chem., 264, 7734 - 7741 (1989): "Characterization of a Novel Isozyme of cGMP-dependent Protein Kinase from Bovine Aorta" |
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3 |
Sekhar, K.R.; Hatchett, R.J.; Shabb, J.B.; Wolfe, L.; Francis, S.H.; Wells, J.W.; Jastorff, B.; Butt, E.; Chakinala, M.M.; Corbin, J.D., Mol. Pharmacol., 42, 103 - 108 (1992): "Relaxation of Pig Coronary Arteries By New and Potent cGMP Analogs That Selectively Activate Type I a Compared to Type I b cGMP-Dependent Protein Kinase" |
1 |
Erneux, C.; Miot, F.; Van Haastert, P.J.M.; Jastorff, B., J. Cyclic Nucleotide Protein Phosphorylation Res., 10, 463 - 472 (1985) : "The Binding of Cyclic Nucleotide Analogs to a Purified Cyclic GMP- Stimulated Phosphodiesterase from Bovine Adrenal Tissue" |
2 |
Braumann, T.; Erneux, C.; Petridis, G.; Stohrer, W.D.; Jastorff, B., Biochim. Biophys. Acta, 871, 199 - 206 (1986) : "Hydrolysis of Cyclic Nucleotides by a Purified cGMP- stimulated Phosphodiesterase: Structural Requirements for Hydrolysis" |
3 |
Beltman, J.; Becker, D.E.; Butt, E.; Jensen, G.S.; Rybalkin, S.D.; Jastorff, B.; Beavo, J.A., Mol. Pharmacol., 47, 330 - 339 (1995): "Characterization of Cyclic Nucleotide Phosphodiesterases With Cyclic GMP Analogs: Topology of the Catalytic Domains" |
4 |
Hebert, M.C.; Schwede, F.; Jastorff, B.; Cote, R. H., J. Biol. Chem., 273, 5557 - 5565 (1998): "Structural Features of the Noncatalytic cGMP Binding Sites of Frog Photoreceptor Phoshodiesterase Using cGMP Analogs" |
1 |
Tanaka, J.C.; Eccleston, J.F.; Furman, R.E., Biochemistry 28, 2776 - 2784 (1989): "Photoreceptor Channel Activation by Nucleotide Derivatives" |
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2 |
Kramer, R.H.; Tibbs, G.R., J. Neurosci., 16, 1285 - 1293 (1996): "Antagonists of Cyclic Nucleotide-gated Channels and Molecular Mapping of their Site of Action" |