Title: Mildiomycin
CAS Registry Number: 67527-71-3
CAS Name: (S)-4-Amino-1-[4-[(2-amino-3-hydroxy-1-oxopropyl)amino]-9-[(aminoiminomethyl)amino]-6-C-carboxy-2,3,4,7,9-pentadeoxy-a-L-talo-non-2-enopyranosyl]-5-(hydroxymethyl)-2(1H)-pyrimidinone
Molecular Formula: C19H30N8O9
Molecular Weight: 514.49
Percent Composition: C 44.36%, H 5.88%, N 21.78%, O 27.99%
Literature References: A nucleoside antibiotic with anti-mildew activity and low toxicity in mammals and fish. Isoln from Streptoverticillium rimofaciens B-98891 and characterization: S. Harada, T. Kishi, J. Antibiot. 31, 519 (1978). Taxonomy and fermentation study: T. Iwasa et al., ibid. 511. Structure: S. Harada et al., J. Am. Chem. Soc. 100, 4895 (1978); Tetrahedron 37, 1317 (1981). Anti-mildew spectrum: K. Suetomi, T. Kusaka, Nippon Noyaku Gakkaishi 4, 349 (1979), C.A. 92, 17012c (1980).
Properties: Hygroscopic solid, mp >300° (monohydrate). [a]D20 +100° (c = 0.5 in water); +78.5° (c = 0.5 in 0.1N HCl). pKa¢: 2.8, 4.3, 7.2, >12. uv max (pH 7 and 0.1N NaOH): 271 nm (E1%1cm 164); (0.1N HCl): 280 nm (E1%1cm 247). LD50 in rats, mice: ~500-1000 mg/kg i.v.; ~2.5-5.0 g/kg orally (Harada, Kishi).
Melting point: mp >300° (monohydrate)
pKa: pKa¢: 2.8, 4.3, 7.2, >12
Optical Rotation: [a]D20 +100° (c = 0.5 in water); +78.5° (c = 0.5 in 0.1N HCl)
Absorption maximum: uv max (pH 7 and 0.1N NaOH): 271 nm (E1%1cm 164); (0.1N HCl): 280 nm (E1%1cm 247)
Toxicity data: LD50 in rats, mice: ~500-1000 mg/kg i.v.; ~2.5-5.0 g/kg orally (Harada, Kishi) |