Title: Puromycin
CAS Registry Number: 53-79-2
CAS Name: 3¢-[[(2S)-2-Amino-3-(4-methoxyphenyl)-1-oxopropyl]amino]-3¢-deoxy-N,N-dimethyladenosine
Additional Names: L-3¢-(a-amino-p-methoxyhydrocinnamamido)-3¢-deoxy-N,N-dimethyladenosine; 6-dimethylamino-9-[3-deoxy-3-(p-methoxy-L-phenylalanylamino)-b,D-ribofuranosyl]-b-purine; 6-dimethylamino-9-[3¢-(p-methoxy-L-phenylalanylamino)-3¢-deoxy-b,D-ribofuranosyl]purine; stylomycin
Manufacturers' Codes: CL-13900; P-638; 3123-L
Molecular Formula: C22H29N7O5
Molecular Weight: 471.51
Percent Composition: C 56.04%, H 6.20%, N 20.79%, O 16.97%
Literature References: Aminonucleoside antibiotic produced by the soil actinomycete Streptomyces alboniger. Structural analog of aminoacyl-tRNA; inhibits protein synthesis. Isoln: J. N. Porter et al., Antibiot. Chemother. 2, 409 (1952); eidem, US 2763642 (1956 to Am. Cyanamid). Structure: C. W. Waller et al., J. Am. Chem. Soc. 75, 2025 (1953); P. W. Fryth et al., ibid. 80, 2736 (1958). Synthesis: B. R. Baker et al., ibid. 76, 4044 (1954); 77, 12 (1955); M. J. Robins et al., J. Org. Chem. 66, 8204 (2001). Conformation: O. Jardetzky, J. Am. Chem. Soc. 85, 1823 (1963). Effect on protein synthesis: D. Nathans, Proc. Natl. Acad. Sci. USA 51, 585 (1964). Use in gene transfer studies: S. de la Luna et al., Gene 62, 121 (1988). Review: D. Nathans in Antibiotics vol. I, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 259-277.
Properties: Crystals from water, mp 175.5-177°. [a]D25 -11° (ethanol). uv max (0.1N NaOH): 275 nm (e 20300); in 0.1N HCl: 267.5 nm (e 19500). pKa: 6.8, 7.2. Sparingly sol in water, organic solvents. LD50 in mice (mg/kg): 350 i.v.; 525 i.p.; 675 orally (Porter, 1952).
Melting point: mp 175.5-177°
pKa: pKa: 6.8, 7.2
Optical Rotation: [a]D25 -11° (ethanol)
Absorption maximum: uv max (0.1N NaOH): 275 nm (e 20300); in 0.1N HCl: 267.5 nm (e 19500)
Toxicity data: LD50 in mice (mg/kg): 350 i.v.; 525 i.p.; 675 orally (Porter, 1952)
Derivative Type: Dihydrochloride
CAS Registry Number: 58-58-2
Molecular Formula: C22H29N7O5.2HCl
Molecular Weight: 544.43
Percent Composition: C 48.53%, H 5.74%, N 18.01%, O 14.69%, Cl 13.02%
Properties: White crystals or powder. Prepd as the dihydrate, mp 174° (dec). Sol in water.
Melting point: mp 174° (dec)
Use: Research tool for studying protein synthesis; cell line selection agent in gene transfer experiments. |