Title: Cyclic AMP
CAS Registry Number: 60-92-4
CAS Name: Adenosine cyclic 3￠,5￠-(hydrogen phosphate)
Synonyms: adenosine 3￠,5￠-cyclic monophosphate; adenosine 3￠,5￠-cyclic phosphate; adenosine 3￠,5￠-monophosphate; adenosine 3￠,5￠-phosphate; cyclic adenosine 3￠,5￠-monophosphate; acrasin; 3￠,5￠-AMP; cAMP
Molecular Formula: C10H12N5O6P
Molecular Weight: 329.21
Percent Composition: C 36.48%, H 3.67%, N 21.27%, O 29.16%, P 9.41%
Literature References: Key intracellular regulator of a number of cellular processes; found in most animal cells, in bacteria, and in some higher plants. First isoln and identification: Rall
et al., J. Biol. Chem. 224, 463 (1957); Sutherland, Rall,
ibid. 232, 1077 (1958). Molecular structure and conformation: Cook
et al., J. Am. Chem. Soc. 79, 3607 (1957); Lipkin
et al., ibid. 81, 6198 (1959); Watenpaugh
et al., Science 159, 206 (1968). Syntheses: Smith
et al., J. Am. Chem. Soc. 83, 698 (1961); Borden, Smith,
J. Org. Chem. 31, 3247 (1966). Physical data: D. Lipkin
et al., J. Am. Chem. Soc. 81, 6075 (1959). Functions as a mediator of hormone-action for a variety of hormones such as epinephrine, glucagon and ACTH,
q.q.v. Activates phosphorylation of proteins by protein kinases. Defined as a "second messenger" because of its response to hormones ("first messengers"). Converted from adenosine triphosphate (ATP) by the enzyme
adenylate cyclase. Deactivated by
cyclic nucleotide phosphodiesterases which convert it to 5￠-adenylic acid. Reviews of biochemical model: Sutherland
et al., J. Biol. Chem. 237, 1220-1243 (1962); Robison
et al., Annu. Rev. Biochem. 37, 149 (1968); Jost, Rickenberg,
ibid. 40, 741 (1971); Sutherland,
J. Am. Med. Assoc. 214, 1281 (1970); Pastan, Perlman,
Nature New Biol. 229, 5 (1971); G. A. Robison
et al., Eds.,
Ann. N.Y. Acad. Sci. 185, (1971); Losert,
Pharmazie 28, 351 (1973).
See also Cyclic GMP. Identity with acrasin from cellular slime molds (
Dictyostelium species), where it acts as a "first" rather than a "second messenger": Konijn
et al., Proc. Natl. Acad. Sci. USA 58, 1152 (1967). Review of quantitative methods:
Methods in Molecular Biology vol. 3, "Methods in Cyclic Nucleotide Research", Mark Chasin, Ed. (Marcel Dekker, New York, 1972). Books: G. A. Robison
et al., Cyclic AMP (Academic Press, New York, 1971);
Advan. Cyclic Nucleotide Res. vols. 1, 2, 3, P. Greengard, G. A. Robison, Eds. (Raven Press, New York, 1972, 1973);
Handb. Exp. Pharmacol. 58, "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.
Properties: Hydrate crystallizes from water as platelets with pearly luster, mp 219-220° (with gas evolution). [a]D -51.3° (c = 0.67). uv max (pH 2): 256 nm (e 14500); (pH 7): 258 nm (e 14650). Heat stable; resistant to inactivation by acid or alkali. Found in concns of 10-7 to 10-6 moles/kg in living cells.
Melting point: mp 219-220° (with gas evolution)
Optical Rotation: [a]D -51.3° (c = 0.67)
Absorption maximum: uv max (pH 2): 256 nm (e 14500)
