5'-Adenylic Acid
Title: 5¢-Adenylic Acid
CAS Registry Number: 61-19-8
Additional Names: Muscle adenylic acid; ergadenylic acid; t-adenylic acid; adenosine 5¢-monophosphate; adenosine phosphate; adenosine-5¢-phosphoric acid; adenosine-5¢-monophosphoric acid; A-5MP; AMP
Manufacturers' Codes: NSC-20264
Trademarks: Adényl (Am. Home)
Molecular Formula: C10H14N5O7P
Molecular Weight: 347.22
Percent Composition: C 34.59%, H 4.06%, N 20.17%, O 32.25%, P 8.92%
Literature References: Nucleotide; widely distributed in nature. Prepn from tissues: Embden, Zimmerman, Z. Physiol. Chem. 167, 137 (1927); Embden, Schmidt, ibid. 181, 130 (1929); cf. Kalckar, J. Biol. Chem. 167, 445 (1947). Prepn by hydrolysis of ATP with barium hydroxide: Kerr, J. Biol. Chem. 139, 131 (1941). Synthesis: Baddiley, Todd, J. Chem. Soc. 1947, 648. Commercial prepn by enzymatic phosphorylation of adenosine. Monograph on synthesis of nucleotides: G. R. Pettit, Synthetic Nucleotides vol. 1 (Van Nostrand-Reinhold, New York, 1972) 252 pp. Crystal structure: Kraut, Jensen, Acta Crystallogr. 16, 79 (1963). Reviews: see Adenosine.
Properties: Crystals from water + acetone, mp 196-200°. [a]D20 -47.5° (c = 2, 2% NaOH); [a]D20 -26.0° (c = 2, 10% HCl). pK1 = 3.8; pK2 = 6.2. uv max (pH 7.0): 259 nm (aM 15.4 ´ 103). Readily sol in boiling water. The compound is readily deaminated by nitrous acid to form inosinic acid; less rapidly hydrolyzed than 3¢-adenylic acid by sulfuric acid. Furfural is formed only in traces on distillation with 20% HCl, cf. Levene, Bass, Nucleic Acids (New York, 1931) pp 230-232.
Melting point: mp 196-200°
pKa: pK1 = 3.8; pK2 = 6.2
Optical Rotation: [a]D20 -47.5° (c = 2, 2% NaOH); [a]D20 -26.0° (c = 2, 10% HCl)
Absorption maximum: uv max (pH 7.0): 259 nm (aM 15.4 ´ 103)
Therap-Cat: Nutrient.

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