Title: Cyclic GMP
CAS Registry Number: 7665-99-8
CAS Name: Guanosine cyclic 3￠,5￠-(hydrogen phosphate)
Synonyms: cyclic guanosine 3￠,5￠-monophosphate; guanosine 3￠,5￠-cyclic monophosphate; guanosine 3￠,5￠-cyclic phosphate; guanosine 3￠,5￠-monophosphate; 3￠,5￠-GMP; cGMP
Molecular Formula: C10H12N5O7P
Molecular Weight: 345.21
Percent Composition: C 34.79%, H 3.50%, N 20.29%, O 32.44%, P 8.97%
Literature References: A cellular regulatory agent which has been described as a "second messenger".
See Cyclic AMP. First synthesized because of the interest in cyclic nucleotides generated by cyclic AMP: Smith
et al., J. Am. Chem. Soc. 83, 698 (1961); Borden, Smith,
J. Org. Chem. 31, 3247 (1966). Has subsequently been found in animal and bacterial cells in concentrations of 10-8 to 10-6 moles/kg. First isoln from rat urine: Ashman
et al., Biochem. Biophys. Res. Commun. 11, 330 (1963). Structure and conformation: Chwang, Sundaralingam,
Nature New Biol. 244, 136 (1973). Proposed as an antagonist of cyclic AMP in bidirectional systems such as contraction-relaxation or glycogen synthesis-glycogen breakdown. Cyclic GMP levels increase in response to a variety of hormones including acetylcholine, insulin and oxytocin. Formed by conversion of guanosine triphosphate by the enzyme
guanylate cyclase and hydrolyzed by cyclic nucleotide phosphodiesterases. Found to activate specific protein kinases. Reviews of biochemical model: Goldberg
et al., in
Pharmacology and the Future of Man vol. 5, R. A. Maxwell, G. H. Acheson, Eds. (Karger, New York, 1973) pp 146-169;
eidem in
Advan. Cyclic Nucleotide Res. vol. 3, P. Greengard, G. A. Robison, Eds. (Raven Press, New York, 1973) pp 155-223; Kolata,
Science 182, 149-151 (1973);
Nature 246, 186 (1973); N. D. Goldberg, M. K. Haddox,
Annu. Rev. Biochem. 46, 823-896 (1977). Book:
Handb. Exp. Pharmacol. 58, entitled "Cyclic Nucleotides", Pt. I: Biochemistry and Pt. II: Physiology & Pharmacology, J. A. Nathanson, J. W. Kobabian, Eds. (Springer-Verlag, New York, 1982) 736 and 1000 pp resp.
Derivative Type: Calcium salt
Molecular Formula: C20H22CaN10O14P2
Molecular Weight: 728.47
Percent Composition: C 32.98%, H 3.04%, Ca 5.50%, N 19.23%, O 30.75%, P 8.50%
Properties: Decahydrate. uv max (pH 1): 256.5 nm (e 11350); (pH 7): 254 nm (e 12950); (pH 12): 262 nm (e 12400).
Absorption maximum: uv max (pH 1): 256.5 nm (e 11350); (pH 7): 254 nm (e 12950); (pH 12): 262 nm (e 12400)
