2787. 2′-Cytidylic Acid

Nomenclature

CAS number: 85-94-9
Cytidine-2′-monophosphate; cytidylic acid a; 2′-cytidinephosphoric acid; cytidine-2′-phosphate; 2′-cytosylic acid; 2′-CMP.
C9H14N3O8P; mol wt 323.20.
C 33.45%, H 4.37%, N 13.00%, O 39.60%, P 9.58%.

Description and references

Ribonuclease inhibitor. Prepn from yeast ribonucleic acid: Cohn, Carter, J. Am. Chem. Soc. 72, 2606 (1950); Loring et al., J. Biol. Chem. 196, 807 (1952); by phosphorylation of N6,O3′,O5′-tribenzoylcytidine: Rammler, Khorana, J. Am. Chem. Soc. 84, 3112 (1962). Crystal structure and conformation of the trihydrate: Kartha et al., Science 179, 495 (1973). Reviews: See Cytidine.

Chemical structure

Properties

Crystals, dec 238-240°. [α]D20 +20.7° (water); [α]D25 -3° (aq NaOH adjusted to pH 10). uv max at pH 2: 278 nm (ε 12.7); at pH 12: 272 nm (ε 8.6). pKa1 0.8; pKa2 4.36; pKa3 6.17. Sparingly sol in water. Less sol than 3′-cytidylic acid.