Sinefungin
Title: Sinefungin
CAS Registry Number: 58944-73-3
CAS Name: 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-D-glycero-a-L-talo-decofuranuronic acid
Additional Names: Compd 57926; Antibiotic 32232RP
Manufacturers' Codes: A-9145
Molecular Formula: C15H23N7O5
Molecular Weight: 381.39
Percent Composition: C 47.24%, H 6.08%, N 25.71%, O 20.98%
Literature References: Adenine-containing antibiotic produced by Streptomyces griseoleus NRRL 3739. Isoln: R. L. Hamill, M. M. Hoehn, US 3758681 (1973 to Lilly); eidem, J. Antibiot. 26, 463 (1973). Antifungal activity: R. S. Gordee, T. F. Butler, ibid. 466. Antiprotozoal activity: D. K. Dube et al., Am. J. Trop. Med. Hyg. 32, 31 (1983); A. Ferrante et al., Trans. R. Soc. Trop. Med. Hyg. 78, 837 (1984); P. Paolantonacci et al., Antimicrob. Agents Chemother. 28, 528 (1985); E. Zweygarth et al., Trop. Med. Parasitol. 37, 255 (1986); in vivo antileishmanial activity: J. L. Avila et al., Am. J. Trop. Med. Hyg. 43, 139 (1990). Synthesis: M. Geze et al., J. Am. Chem. Soc. 105, 7638 (1983); stereoselective synthesis: M. P. Maguire et al., J. Org. Chem. 55, 948 (1990). Inhibition of methyltransferase: R. T. Borchardt et al., Biochem. Biophys. Res. Commun. 89, 919 (1979).
Properties: White powder. Sol in water, very slightly sol in methanol and ethanol. Insol in organic solvents. Stable at room temp in aq soln from pH 1 to 11. pKa (66% DMF): 2.9, 3.9, 8.9, 10.2. uv max in neutral solns: 206 nm, 258 nm (E1cm1% 520, 325); in basic solns: 256 nm (E1cm1% 325). [a]D25 -2.61° (c = 5 in water). Also reported as [a]D23 +12 ±2° (c = 0.227 in water). LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)
pKa: pKa (66% DMF): 2.9, 3.9, 8.9, 10.2
Optical Rotation: [a]D25 -2.61° (c = 5 in water); [a]D23 +12 ±2° (c = 0.227 in water)
Absorption maximum: uv max in neutral solns: 206 nm, 258 nm (E1cm1% 520, 325)
Toxicity data: LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)

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