Title: Calcimycin
CAS Registry Number: 52665-69-7
CAS Name: 5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid
Additional Names: antibiotic A-23187
Manufacturers' Codes: A-23187
Molecular Formula: C29H37N3O6
Molecular Weight: 523.62
Percent Composition: C 66.52%, H 7.12%, N 8.02%, O 18.33%
Literature References: Polyether antibiotic produced by a strain of Streptomyces chartreusensis Calhoun and Johnson NRRL 3882. Activity as a divalent cation ionophore in isolated mitochondria: P. W. Reed, H. A. Lardy, J. Biol. Chem. 247, 6970 (1972). Prepn and antimicrobial activity: R. M. Gale et al., US 3923823 (1975 to Lilly). Elucidation of structure: M. O. Chaney et al., J. Am. Chem. Soc. 96, 1932 (1974). Spectral studies of ionophore and metal ion complexes: D. R. Pfeiffer et al., Biochemistry 13, 4007 (1974). Total synthesis and absolute configuration: D. A. Evans et al., J. Am. Chem. Soc. 101, 6789 (1979); P. A. Grieco et al., J. Org. Chem. 45, 3537 (1980). Stereospecific synthesis: G. R. Martinez et al., J. Am. Chem. Soc. 104, 1436 (1982); D. P. Negri, Y. Kishi, Tetrahedron Lett. 28, 1063 (1987). Review of cation binding and transport properties: D. R. Pfeiffer et al., Ann. N.Y. Acad. Sci. 307, 402-423 (1978). Use in model systems of calcium transport: M. Takamori et al., J. Neurol. Sci. 50, 89 (1981); M. Takamori et al., ibid. 51, 207 (1981); M. H. Freedman et al., Cell. Immunol. 58, 134 (1981); G. Thomas, Eur. J. Pharmacol. 81, 35 (1982); V. L. Lew, J. Garcia-Sancho, Cell Calcium 6, 15 (1985).
Properties: Crystalline solid, mp 181-182°. [a]D25 -56° (c = 1 in chloroform). uv max (ethanol): 204, 225, 278, 378 nm (E 28200, 26200, 18200, 8200). pKa1 6.9 in 90% DMSO. Slightly sol in water, readily sol in ethyl acetate, chloroform, methanol, DMSO. Also reported as mp 184.5-186° (Evans, 1979). LD50 i.p. in mice: 10 mg/kg (Gale).
Melting point: mp 181-182°; mp 184.5-186° (Evans, 1979)
pKa: pKa1 6.9 in 90% DMSO
Optical Rotation: [a]D25 -56° (c = 1 in chloroform)
Absorption maximum: uv max (ethanol): 204, 225, 278, 378 nm (E 28200, 26200, 18200, 8200)
Toxicity data: LD50 i.p. in mice: 10 mg/kg (Gale)
Derivative Type: Mixed calcium-magnesium salt
Properties: Colorless crystalline solid, mp 230-250° (dec). uv max (ethanol, neutral): 202, 228, 303, 370 nm (E1%1cm 425, 490, 278, 109). Insol in water, pentane, hexane, heptane. Very slightly sol in methanol, DMSO. Very sol in methylene chloride, chloroform, acetone, methyl ethyl ketone, diethyl ketone, ethyl acetate.
Melting point: mp 230-250° (dec)
Absorption maximum: uv max (ethanol, neutral): 202, 228, 303, 370 nm (E1%1cm 425, 490, 278, 109)
Use: Biochemical tool used to study the role of divalent cations in various biological systems. |