157. 3′-Adenylic Acid

Nomenclature

CAS number: 84-21-9
Adenosine 3′-monophosphate; adenosine-3′-phosphoric acid; adenosine-3′-monophosphoric acid; adenylic acid b; yeast adenylic acid; synadenylic acid; h-adenylic acid.
C10H14N5O7P; mol wt 347.22.
C 34.59%, H 4.06%, N 20.17%, O 32.25%, P 8.92%.

Description and references

Early prepns from yeast nucleic acid: Levene, Bass, Nucleic Acids (Chemical Catalogue Co., New York, 1931). Early work probably done on mixtures of 2′- and 3′-adenylic acids; both compds isomerize readily to form an equilibrium mixture under acid conditions: Carter, Cohn, Fed. Proc. 8, 190 (1949); Baddily, in The Nucleic Acids vol. 1, E. Chargaff, J. N. Davidson, Eds. (Academic Press, New York, 1955) pp 165-168; A. M. Michelson, The Chemistry of Nucleosides and Nucleotides (Academic Press, New York, 1963) pp 100-106. Synthesis: Brown, Todd, J. Chem. Soc. 1952, 44. Structure of dihydrate: Brown et al., Nature 172, 1184 (1953); Sundaralingam, Acta Crystallogr. 21, 495 (1966). Reviews: see Adenosine.

Chemical structure

Properties

Long, fine, colorless, needles. mp 197° (dec). Dihydrate, d (calc) 1.698. Absorption spectrum: Voet et al., Biopolymers 1, 193 (1963). Difficultly sol in boiling water. Gives quantitative yield of furfural when distilled with 20% HCl for 3 hrs (different from 5′-adenylic acid which yields only traces). cf. Hoffman, J. Biol. Chem. 73, 15 (1927); Embden, Schmidt, Z. Physiol. Chem. 181, 130 (1929).