Blasticidin S
Title: Blasticidin S
CAS Registry Number: 2079-00-7
CAS Name: 4-[[3-Amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-b-D-erythro-hex-2-enopyranuronic acid
Additional Names: 4-[3-amino-5-(1-methylguanidino)valeramido]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-b-D-erythro-hex-2-enopyranuronic acid; 1-(1¢-cytosinyl)-4-[L-3¢-amino-5¢-(1¢¢-N-methylguanidino)-valerylamino]-1,2,3,4-tetradeoxy-b-D-erythro-hex-2-enuronic acid
Molecular Formula: C17H26N8O5
Molecular Weight: 422.44
Percent Composition: C 48.33%, H 6.20%, N 26.53%, O 18.94%
Literature References: Nucleoside antibiotic produced by Streptomyces griseochromogenes: Isoln and antimicrobial activity: Takeuchi et al., J. Antibiot. 11A, 1 (1958); Sumiki, Umezawa, JP 60 16449 (1960 to Japan Antibiot. Res. Assoc.), C.A. 55, 21474e (1961). Structure: Otake et al., Agric. Biol. Chem. 30, 132 (1966); Fox, Watanabe, Tetrahedron Lett. 1966, 897. Abs config: Yonehara et al., ibid. 1966, 3785. Synthesis of the unsaturated carbohydrate: Goody et al., ibid. 1970, 293; of the cytosinine moiety: Fox, Watanabe, Pure Appl. Chem. 28, 475 (1971); Kondo et al., Tetrahedron Lett. 1972, 1881; eidem, Tetrahedron 29, 1801 (1973). Crystal and molecular structure: V. Swaminathan et al., Biochim. Biophys. Acta 655, 335 (1981).
Properties: Needles from water, dec 235-236°. [a]D11 +108.4° (water). uv max (0.1N HCl): 275 nm (E1%1cm 349); (0.1N NaOH): 266-270 nm (E1%1cm 266). Sol in water, acetic acid. Practically insol in methanol, ethanol, acetone, benzene, ether, ethyl acetate, chloroform, carbon tetrachloride, cyclohexane, xylene, pyridine, dioxane. LD50 i.v. in mice: 2.82 mg/kg (Takeuchi).
Optical Rotation: [a]D11 +108.4° (water)
Absorption maximum: uv max (0.1N HCl): 275 nm (E1%1cm 349); (0.1N NaOH): 266-270 nm (E1%1cm 266)
Toxicity data: LD50 i.v. in mice: 2.82 mg/kg (Takeuchi)
 
Derivative Type: Hydrochloride
Properties: Crystals, dec 224-225°.
 
Use: Antifungal against rice blast disease in Japan.

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