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Analogues for Characterization of cyclic GMP Binding Proteins

Fig. 1: Positions for the chemical modification of cyclic GMP

Meaningful selected analogues of cyclic GMP are extremely useful for mapping studies of different cGMP receptor proteins in order to get information about the essential corresponding molecular forces and their positions in the cyclic GMP moiety:

Besides important insights in the binding principles of the receptor, the practical results of successful mapping studies include the determination of positions where a spacer for affinity chromatography is tolerated, where fluorescent markers can be attached and which chemical modifications are allowed for potential analogues.

BIOLOG offers so many different analogues of cyclic GMP, that modifications for nearly each position of the second messenger are available.

The following table gives examples for analogues suitable for mapping studies:

Position Suitable Analog Effects

Purine N1


Donor/acceptor potential changed

Purine C2

N2-MB-cGMP (inquire)

No hydrogen bonding
H-bonds impaired, steric effects

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 
No hydrogen bonding at 2'-OH, steric effects

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.

Mapping of Protein Kinase G:


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"


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"


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"


Mapping of Cyclic Nucleotide Phosphodiesterases:


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"


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"


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"


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"


Mapping of cGMP-gated Ion Channels :


Tanaka, J.C.; Eccleston, J.F.; Furman, R.E., Biochemistry 28, 2776 - 2784 (1989): "Photoreceptor Channel Activation by Nucleotide Derivatives"


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"