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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Blasticidin S
Blasticidin S.png
CAS number 2079-00-7 YesY
PubChem 258
ChemSpider 148673 YesY
KEGG C02010 YesY
Jmol-3D images Image 1
Molecular formula C17H26N8O5
Molar mass 422.44 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Blasticidin S is an antibiotic that is produced by Streptomyces griseochromogenes. In biological research, specifically genetic engineering, it is used to select transformed cells which have been engineered to carry a resistance gene for blasticidin. In short, DNA of interest is fused to DNA encoding a resistance gene, and then is transformed into cells. After allowing time for recovery and for cells to begin transcribing and translating their new DNA, blasticidin is added. Now only the cells that have the new DNA can grow.