Sparsomycin
Title: Sparsomycin
CAS Registry Number: 1404-64-4
CAS Name: (2E)-N-[(1S)-1-(Hydroxymethyl)-2-[(R)-[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-2-propenamide
Additional Names: (E)-(1S)-1,2,3,4-tetrahydro-N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-6-methyl-2,4-dioxo-5-pyrimidineacrylamide; (+)-sparsomycin
Manufacturers' Codes: NSC-59729; U-19183
Molecular Formula: C13H19N3O5S2
Molecular Weight: 361.44
Percent Composition: C 43.20%, H 5.30%, N 11.63%, O 22.13%, S 17.74%
Literature References: Protein synthesis inhibitor with antibiotic and antitumor activity. Isoln from fermentation broth of Streptomyces sparsogenes var sparsogenes: S. P. Owen et al., Antimicrob. Agents Chemother. 1962, 772; GB 974541 (1964 to Upjohn); from S. cuspidosporus: E. Higashide et al., Takeda Kenkyusho Nempo 25, 1 (1966), C.A. 66, 54238q (1967). Characterization and purification: A. D. Argoudelis, R. R. Herr, Antimicrob. Agents Chemother. 1962, 780. Structural elucidation: P. F. Wiley, F. A. MacKellar, J. Org. Chem. 41, 1858 (1976). Total synthesis: H. C. J. Ottenheijm et al., ibid. 46, 3273 (1981); R. M. J. Liskamp et al., ibid. 5408. HPLC determn in plasma and urine: B. Winograd et al., J. Chromatogr. 275, 145 (1983). Pharmacokinetics and toxicology: Z. Zylicz et al., Cancer Chemother. Pharmacol. 20, 115 (1987). Ribosomal binding studies: E. Lazaro et al., Antimicrob. Agents Chemother. 35, 10 (1991). Biosynthetic studies: R. J. Parry et al., J. Am. Chem. Soc. 114, 5946 (1992). Review of chemistry and biological activity: H. C. J. Ottenheijm et al., Prog. Med. Chem. 23, 220-268 (1986).
Properties: Crystals, mp 208-209° (dec). [a]D25 +69° (c = 0.5 in water). pKa¢ 8.67 in water, 9.05 in 40% ethanol. uv max: 302 nm (water or 0.1N aq sulfuric acid), 328 nm (0.1N aq potassium hydroxide). Slightly sol in water and lower alcohols. Insol in less polar organic solvents. LD50 in dogs, rats, mice (mg/kg): 0.5-1.0, 2.25, 4.32 i.v. (Ottenheijm, 1986). LD50 i.p. in mice: 2.4 mg/kg (Owen).
Melting point: mp 208-209° (dec)
pKa: pKa¢ 8.67 in water, 9.05 in 40% ethanol
Optical Rotation: [a]D25 +69° (c = 0.5 in water)
Absorption maximum: uv max: 302 nm (water or 0.1N aq sulfuric acid), 328 nm (0.1N aq potassium hydroxide)
Toxicity data: LD50 in dogs, rats, mice (mg/kg): 0.5-1.0, 2.25, 4.32 i.v. (Ottenheijm, 1986); LD50 i.p. in mice: 2.4 mg/kg (Owen)
Use: Research tool for studying protein biosynthesis.

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