Title: Tubercidin

CAS Registry Number: 69-33-0

CAS Name: 7-b-D-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Additional Names: 4-amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine; 7-deazaadenosine; sparsamycin A

Manufacturers' Codes: U-10071

Molecular Formula: C11H14N4O4

Molecular Weight: 266.25

Percent Composition: C 49.62%, H 5.30%, N 21.04%, O 24.04%

Literature 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.

Properties: Needles from water, dec 247-248°. [a]D17 -67° (50% acetic acid). uv max (0.01N NaOH): 270 nm (e 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).

Optical Rotation: [a]D17 -67° (50% acetic acid)

Absorption maximum: uv max (0.01N NaOH): 270 nm (e 12,100)

Toxicity data: LD50 i.v. in mice: 45 mg/kg (Anzai)