Title: Methymycin
CAS Registry Number: 497-72-3
Molecular Formula: C25H43NO7
Molecular Weight: 469.61
Percent Composition: C 63.94%, H 9.23%, N 2.98%, O 23.85%
Literature References: Antibiotic substance produced by a streptomycete from soil near Oswego, N.Y. Has a macrolide structure (12-membered lactone ring, compare Picromycin). Isoln and antibacterial activity: Donin et al., Antibiot. Annu. 1, 179 (1953-4). Production using Streptomyces venezuelae cultures: Dutcher et al., US 2916483 (1959 to Olin Mathieson). Structure: C. Djerassi, J. A. Zderic, J. Am. Chem. Soc. 78, 6390 (1956). Absolute configuration: Rickards, Smith, Tetrahedron Lett. 1970, 1025; Manwaring et al., ibid. 1029. Biosynthesis: Birch et al., J. Chem. Soc. 1964, 5274. Synthesis: Masamune et al., J. Am. Chem. Soc. 97, 3512 (1975). Possible mechanism of action: Wilhelm et al., Antimicrob. Agents Chemother. 1967, 236.
Properties: Prisms from abs ethanol, mp 195.5-197°. [a]D22 +61° (c = 0.7 in methanol), +74° (c = 1.1 in chloroform). Basic substance, pKb¢ 5.7. uv max (methanol): 223, 322 nm (e 10500, 47). Very slightly sol in water, hexane. Sol in methanol, acetone, chloroform, dil acids. Moderately sol in ethanol, ether.
Melting point: mp 195.5-197°
pKa: pKb¢ 5.7
Optical Rotation: [a]D22 +61° (c = 0.7 in methanol), +74° (c = 1.1 in chloroform)
Absorption maximum: uv max (methanol): 223, 322 nm (e 10500, 47)
Derivative Type: Sulfate
Molecular Formula: (C25H43NO7)2.H2SO4
Molecular Weight: 1037.30
Percent Composition: C 57.89%, H 8.55%, N 2.70%, O 27.76%, S 3.09%
Properties: Crystals from methanol + acetone. Sol in water, methanol.
Derivative Type: Acid sulfate
Molecular Formula: C25H43NO7.H2SO4
Molecular Weight: 567.69
Percent Composition: C 52.89%, H 7.99%, N 2.47%, O 31.00%, S 5.65%
Properties: Plates from acetone. Sol in water, acetone.
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