9562. Toyocamycin

Nomenclature

CAS number: 606-58-6
4-Amino-7-β-d-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile; 4-amino-5-cyano-7-(d-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine; uramycin B; vengicide; antibiotic 1037; E-212.
C12H13N5O4; mol wt 291.26.
C 49.48%, H 4.50%, N 24.05%, O 21.97%.

Description and references

Antibiotic substance extracted from the culture filtrate and mycelium of Streptomyces toyocaensis. Isoln: Nishimura et al., J. Antibiot. 9A, 60 (1956). Structure: Ohkuma, ibid. 14A, 343 (1961). Synthesis of aglycone: Taylor, Hendess, J. Am. Chem. Soc. 86, 951 (1964). Total synthesis: Tolman et al., ibid. 90, 524 (1968); 91, 2102 (1969). Biosynthesis: Uematsu, Suhadolnik, Biochemistry 9, 1260 (1970); eidem, J. Biol. Chem. 245, 4365 (1970). Crystal and molecular structure: P. Prusiner, M. Sundaralingam, Acta Crystallogr. B34, 517 (1978).

Chemical structure

Properties

Fine needles from methanol or acetone, mp 243°. Recrystallization from water yields the hydrate, C12H13N5O4.H2O, mp 239-243°. [α]D16 45.7° (c = 1.05 in 0.1N HCl). uv max (H2O): 230, 277 nm (E1%1cm 400, 548). Soluble in acetic acid, acidic solns. Moderately sol in methanol, ethanol, acetone, dioxane, butanol, water, ether. Practically insol in chloroform, ethyl acetate, petr ether. LD100 s.c. in mice: 10-20 mg/kg (Nishimura).