397. Amicetin

Nomenclature

CAS number: 17650-86-1
4-[[(2S)-2-Amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-α-d-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]benzamide.
C29H42N6O9; mol wt 618.68.
C 56.30%, H 6.84%, N 13.58%, O 23.27%.

Description and references

Antibiotic substance produced by Streptomyces vinaceus-drappus isolated from soil near Kalamazoo, Mich.: C. DeBoer et al., J. Am. Chem. Soc. 75, 499 (1953); J. W. Hinman et al., ibid. 5864; McKormich, Hoehn, Antibiot. Chemother. 3, 718 (1953). Chemistry: E. H. Flynn et al., J. Am. Chem. Soc. 75, 5867 (1953). Structural studies: C. L. Stevens et al., J. Org. Chem. 27, 2991 (1962). Configuration: S. Hanessian, T. H. Haskell, Tetrahedron Lett. 5, 2451 (1964). Inhibition of protein synthesis: A. Bloch, C. Coutsogeorgopoulos, Biochemistry 5, 3345 (1966). Binding to 23S rRNA as mechanism of inhibition of peptide bond formation: I. G. Leviev et al., EMBO J. 13, 1682 (1994).

Chemical structure

Properties

Colorless granular crystals, mp 244-245°. pKa = 10.4, 7.0. [α]D24 +116.5° (c = 0.5 in 0.1N HCl). uv max in water: 305 nm (E1%1cm 465); in 0.1N HCl: 316 nm (E1%1cm 433); in 0.1N NaOH: 322 nm (E1%1cm 470). Soly in water at 25° = 2 mg/ml. Slightly sol in common organic solvents. LD50 of citrate complex, pH 6 (mg/kg) in mice: ≈90 i.v., 600-700 s.c.; in rats: ≈200 i.v., ≈600 s.c. (DeBoer).