Title: Gougerotin
CAS Registry Number: 2096-42-6
CAS Name: 1-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,4-dideoxy-4-[[N-(N-methylglycyl)-D-seryl]amino]-b-D-glucopyranuronamide
Additional Names: 1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,4-dideoxy-4-[D-2-[2-(methylamino)acetamido]hydracrylamido]glucopyranuronamide; 1-[4-deoxy-4-(sarcosyl-D-seryl)amino-b-D-glucopyranuronamide]cytosine; aspiculamycin; asteromycin
Molecular Formula: C16H25N7O8
Molecular Weight: 443.41
Percent Composition: C 43.34%, H 5.68%, N 22.11%, O 28.87%
Literature References: Antibiotic substance with antibacterial and antineoplastic activity. Isoln from Streptomyces gougerotii: Kanzaki et al., J. Antibiot. 15A, 93 (1962). Identity with asteromycin: Ikeuchi et al., ibid. 25, 548 (1972). Structure: Iwasaki, Yakugaku Zasshi 82, 1358 (1962). Revised structure: Fox et al., Tetrahedron Lett. 1968, 6029; Watanabe et al., Chem. Pharm. Bull. 17, 416 (1969). Total synthesis: eidem, J. Am. Chem. Soc. 94, 3272 (1972); Lichtenthaler et al., Tetrahedron Lett. 1975, 3527. Identity with aspiculamycin: Lichtenthaler et al., ibid. 665. Mechanism of action study: J. C. Lacal et al., J. Antibiot. 33, 441 (1980). Reviews: Clark in Antibiotics vol. 1, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 278-282; Yukioka, ibid. vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (1975) pp 448-458.
Properties: Needles, mp 211-217° (dec). [a]D27 +53° (c = 0.8). uv max (water): 267, 235 nm (e 9400, 9300); in 0.1N HCl: 275 nm (e 13600); in 0.1N NaOH: 267 nm (e 9800). LD50 in mice (mg/kg): 57 i.v. (Kanzaki).
Melting point: mp 211-217° (dec)
Optical Rotation: [a]D27 +53° (c = 0.8)
Absorption maximum: uv max (water): 267, 235 nm (e 9400, 9300); in 0.1N HCl: 275 nm (e 13600); in 0.1N NaOH: 267 nm (e 9800)
Toxicity data: LD50 in mice (mg/kg): 57 i.v. (Kanzaki) |