3101. Dideoxyadenosine

Nomenclature

CAS number: 4097-22-7
2′,3′-Dideoxyadenosine; 6-amino-9-(2′,3′-dideoxy-β-d-glycero-pentofuranosyl)purine; ddA; ddAdo.
C10H13N5O2; mol wt 235.24.
C 51.06%, H 5.57%, N 29.77%, O 13.60%.

Description and references

Purine nucleoside reverse transciptase inhibitor (NRTI). Prepn: M. J. Robins, R. K. Robins, J. Am. Chem. Soc. 86, 3585 (1964); G. L. Tong et al., J. Org. Chem. 30, 2854 (1965); J. R. McCarthy et al., J. Am. Chem. Soc. 88, 1549 (1966). Chain-terminating inhibition of DNA synthesis: L. Toji, S. S. Cohen, Proc. Natl. Acad. Sci. USA 63, 871 (1969). Antiviral activity vs HIV-1: H. Mitsuya, S. Broder, ibid. 83, 1911 (1986). HPLC determn in biological fluids: P. A. Blau et al., J. Chromatogr. 420, 1 (1987).

Chemical structure

Properties

Crystals from ethanol, mp 184-186°. [α]D25 -25.2° (c = 1.01 in water). uv max in methanol: 259.5 nm (ε 14800).

Derivative

5′-Triphosphate.

Nomenclature

CAS number: 24027-80-3
ddATP.
C10H16N5O11P3; mol wt 475.18.
C 25.28%, H 3.39%, N 14.74%, O 37.04%, P 19.55%.

Description and references

Active metabolite of didanosine, q.v. RIA determn in blood cells: C. Le Saint et al., Antimicrob. Agents Chemother. 48, 589 (2004).

Properties

uv max: 261 nm (ε 15200).

Use

Triphosphate in DNA sequencing as 3′-end chain terminator.

Therapeutic Category

Antiretroviral.

Keywords

Antiretroviral; Reverse Transcriptase Inhibitors; Nucleosides/Nucleotides; Reverse Transcriptase Inhibitor