Title: Mikamycin
Literature References: Antibiotic complex isolated from Streptomyces mitakaensis found in the soil at Mitaka City, Japan. One of the streptogramins, contains 2 major active components mikamycin A (macrolactone) and B (depsipeptide). Isoln and characterization: Arai, Nakamura et al., J. Antibiot. 9A, 193 (1956); Arai, Karasawa et al., ibid. 11A, 14 (1958); Arai, Okabe et al., ibid. 21; Okabe, ibid. 12A, 86 (1959). Both components exhibit synergistic action in vitro and in vivo: Tanaka et al., ibid. 12A, 290 (1959); Watanabe, ibid. 13A, 62 (1960). Production of mikamycin A and B: FR 1349946; Watanabe, US 3137640 (both 1964 to Kanegafuchi). Nomenclature: P. Crooy, R. De Neys, J. Antibiot. 25, 371 (1972). Review: N. Tanaka in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 487-497.
Derivative Type: Mikamycin A see Virginiamycin M1
Derivative Type: Mikamycin B
Additional Names: 4-[4-(Dimethylamino)-N-methyl-L-phenylalanine]virginamycin S1; mikamycin IA; ostreogrycin B; streptogramin B; pristinamycin IA; vernamycin Ba
Molecular Formula: C45H54N8O10
Molecular Weight: 866.96
Percent Composition: C 62.34%, H 6.28%, N 12.92%, O 18.45%
Literature References: Isoln and properties: Watanabe et al., J. Antibiot. 12A, 112 (1959); 13A, 57 (1960). Structure: ibid. 13A, 291, 293 (1960); 14A, 14 (1961); Cox et al., Chem. Commun. 1970, 1623.
Properties: Monohydrate, platelets from methanol, mp 160°. Anhydr form obtained by drying at 150° under vacuum for 16 hrs, dec 262-263°. uv max (methanol): 209, 260, 305 nm (E1%1cm 605, 220, 101). [a]D20 -60.3° (c = 1.0 in methanol). Sol in methanol, ethanol, acetone, butyl acetate, benzene, chloroform. Practically insol in water, petr ether, hexane. Stable at neutral and acid pH, unstable at alkaline pH.
Melting point: mp 160°
Optical Rotation: [a]D20 -60.3° (c = 1.0 in methanol)
Absorption maximum: uv max (methanol): 209, 260, 305 nm (E1%1cm 605, 220, 101)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.
Status: This monograph has been retired and is no longer subject to revision or update. |