Adenosine Triphosphate
Title: Adenosine Triphosphate
CAS Registry Number: 56-65-5
CAS Name: Adenosine 5¢-(tetrahydrogen triphosphate)
Additional Names: ATP; adenosine 5¢-triphosphoric acid
Trademarks: Adetol (Kyowa); Atriphos (Biochimica); Striadyne (Am. Home); Triadenyl (Henning)
Molecular Formula: C10H16N5O13P3
Molecular Weight: 507.18
Percent Composition: C 23.68%, H 3.18%, N 13.81%, O 41.01%, P 18.32%
Literature References: Coenzyme valuable in the transfer of phosphate bond energy. Mammalian skeletal muscle at rest contains 350-400 mg ATP per 100 g. Upon stimulation of the muscle the ATP is hydrolyzed to ADP by the myosin-actin complex unless hydrolysis is prevented by injection of magnesium sulfate. Isoln from rabbit muscle: LePage, Biochem. Prep. 1, 5 (1949); cf. Fiske, Subbarow, Science 70, 381 (1929); Lohmann, Biochem. Z. 223, 460 (1931); 254, 381 (1932); Barrenscheen, Filz, ibid. 250, 281 (1932); Kerr, J. Biol. Chem. 139, 121 (1941); Needham, Biochem. J. 36, 113 (1942). Synthetic routes: Tanaka, Honjo, US 3079379 (1963 to Takeda). Reviews of biosynthesis: Racker, Adv. Enzymol. 23, 323-399 (1961); Deamer, J. Chem. Educ. 46, 198-206 (1971). Reviews of nucleotide coenzymes: Bock in The Enzymes vol. 2A, P. D. Boyer et al., Eds. (Academic Press, New York, 2nd ed., 1960) pp 3-38; A. M. Michelson, The Chemistry of Nucleosides and Nucleotides (Academic Press, New York, 1963) pp 153-250; D. W. Hutchinson, Nucleotides and Coenzymes (John Wiley, New York, 1964) pp 36-82.
Properties: Free ATP, isolated as a glass (by treatment of the Ba salt with H2SO4 and treating the concd aq soln with acetone). [a]D22 -26.7° (c = 3.095). uv max (pH 7.0): 259 nm (aM 15.4 ´ 103). Freely sol in water. A 1% aq soln has a pH of about 2 and is stable at 0° for several hrs. ATP is a tetrabasic acid and after hydrolytic cleavage it is hexabasic. It is usually pptd as the dibarium salt with 4 or 6 mols of water of crystn which can be removed by prolonged drying at 100° over P2O5 and in a vacuum. The anhydr salt is stable, but the hydrated salt slowly decomp forming 5¢-adenylic acid and barium pyrophosphate. For use the barium salt is converted to the sodium or potassium salt by treatment with sodium or potassium sulfate in HCl soln. At pH 6.8-7.4 the Na salt is stable in aq soln provided the product is pure. Ba2+ catalyzes breakdown.
Optical Rotation: [a]D22 -26.7° (c = 3.095)
Absorption maximum: uv max (pH 7.0): 259 nm (aM 15.4 ´ 103)
Derivative Type: Disodium salt
CAS Registry Number: 987-65-5
Trademarks: Adetphos (Kowa); Atenen (Tsuruhara); Circulen (Kyorin); Trinosin (Toa Eiyo)
Molecular Formula: C10H14N5Na2O13P3
Molecular Weight: 551.14
Percent Composition: C 21.79%, H 2.56%, N 12.71%, Na 8.34%, O 37.74%, P 16.86%
Use: In biochemical research. To inhibit enzymatic browning of raw edible plant materials, such as sliced apples, potatoes, etc.
Therap-Cat: Coenzyme.

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