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CAS No 2079-00-7 , b-D-erythro-Hex-2-enopyranuronicacid,4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-,(S)-

  • Name: b-D-erythro-Hex-2-enopyranuronicacid,4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-,(S)-
  • Synonyms: D-erythro-Hex-2-enopyranuronic acid,4-[3-amino-5-(1-methylguanidino)valeramido]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-(7CI); Bla-S;b-D-erythro-Hex-2-enopyranuronicacid,4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-,(S)-;BlasticidinS (6CI,8CI);
  • CAS Registry Number:
  • Transport: 3172
  • Melting Point: 235-236ºC
  • Flash Point: °C
  • Boiling Point: °Cat760mmHg
  • Density: 1.61 g/cm3
  • Refractive index: 1.707
  • Safety Statements: Poison by ingestion, skin contact, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx. See other blastomycin entries.
  • Hazard Symbols: T+: Very toxic;
  • Flash Point: °C
  • Molecular Weight: 422.51
  • InChI: InChI=1/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9?,10-,13+,14-/m0/s1
  • Risk Statements: 28
  • Molecular Formula: C17H26 N8 O5
  • Molecular Structure:CAS No:2079-00-7 b-D-erythro-Hex-2-enopyranuronicacid,4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-,(S)-
References of b-D-erythro-Hex-2-enopyranuronicacid,4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-,(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
Synonyms: 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.