Toyocamycin
Title: Toyocamycin
CAS Registry Number: 606-58-6
CAS Name: 4-Amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Additional Names: 4-amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine; uramycin B; vengicide; antibiotic 1037
Manufacturers' Codes: E-212
Molecular Formula: C12H13N5O4
Molecular Weight: 291.26
Percent Composition: C 49.48%, H 4.50%, N 24.05%, O 21.97%
Literature 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).
Properties: Fine needles from methanol or acetone, mp 243°. Recrystallization from water yields the hydrate, C12H13N5O4.H2O, mp 239-243°. [a]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).
Melting point: mp 243°; mp 239-243°
Optical Rotation: [a]D16 -45.7° (c = 1.05 in 0.1N HCl)
Absorption maximum: uv max (H2O): 230, 277 nm (E1%1cm 400, 548)
Toxicity data: LD100 s.c. in mice: 10-20 mg/kg (Nishimura)

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