Title: Psicofuranine
CAS Registry Number: 1874-54-0
CAS Name: 9-b-D-Psicofuranosyl-9H-purin-6-amine
Additional Names: 9b-D-psicofuranosyladenine; 6-amino-9-D-psicofuranosylpurine; angustmycin C
Manufacturers' Codes: U-9586
Molecular Formula: C11H15N5O5
Molecular Weight: 297.27
Percent Composition: C 44.44%, H 5.09%, N 23.56%, O 26.91%
Literature References: Nucleoside antibiotic produced by Streptomyces hygroscopicus var. decoyicus: Eble et al., Antibiot. Chemother. 9, 419 (1959); Yüntsen, J. Antibiot. 11A, 244 (1958); Eble, Lewis, US 3020274 (1962 to Upjohn). Antibacterial and antitumor activity: N. Tanaka et al., J. Antibiot. 14A, 98 (1961). Structure: Schroeder, Hoeksema, J. Am. Chem. Soc. 81, 1767 (1959); Garrett, ibid. 82, 827 (1960). Synthesis: Farkas, Sorm, Collect. Czech. Chem. Commun. 28, 882 (1963); L. A. Aleksandrova, F. W. Lichtenthaler, Nucleic Acids Symp. Ser. 9, 263 (1981). Biosynthesis: Sugimori, Suhadolnik, J. Am. Chem. Soc. 87, 1136 (1965). Inhibits the conversion of xanthosine-5¢-phosphate to guanosine-5¢-phosphate: Slechta, Biochem. Pharmacol. 5, 96 (1960).
Properties: Crystals, dec 212-214°. [a]D25 -68° (dimethylformamide). uv max (0.01N acid): 259 nm (E1%1cm 508); in 0.01N base: 261 nm (E1%1cm 527). Soly at 25° (mg/ml): water 8; methanol 8; ethanol 6; butanol 2; ethyl acetate 0.23.
Optical Rotation: [a]D25 -68° (dimethylformamide)
Absorption maximum: uv max (0.01N acid): 259 nm (E1%1cm 508); in 0.01N base: 261 nm (E1%1cm 527) |