9804. Tubercidin

Nomenclature

CAS number: 69-33-0
7-β-d-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 4-amino-7-β-d-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine; 7-deazaadenosine; sparsamycin A; U-10071.
C11H14N4O4; mol wt 266.25.
C 49.62%, H 5.30%, N 21.04%, O 24.04%.

Description and references

Antibiotic substance produced in the culture broth of Streptomyces tubericidus. Isoln: Anzai et al., J. Antibiot. 10A, 201 (1957). Structure: Susuki, Marumo, ibid. 14A, 34 (1961). Total synthesis: Tolman et al., J. Am. Chem. Soc. 91, 2102 (1969). Crystal structure: Stroud, Acta Crystallogr. 29B, 690 (1973); Abola, Sundaralingham, ibid. 697.

Chemical structure

Properties

Needles from water, dec 247-248°. [α]D17 -67° (50% acetic acid). uv max (0.01N NaOH): 270 nm (ε 12,100). Sol in acidic and alkaline soln. One gram dissolves in 330 ml water, 200 ml methanol, 2000 ml ethanol. Practically insol in acetone, ethyl acetate, chloroform, benzene, petr ether. LD50 i.v. in mice: 45 mg/kg (Anzai).