Title: Nocardicin(s)
Literature References: Monocyclic b-lactam antibiotics with antimicrobial activity which inhibit bacterial cell wall biosynthesis. Nocardicins A, B, C, D, E, F, G have been identified. All are produced by Nocardia uniformis subsp. tsuyamenensis, A being the most important component. Prodn: H. Aoki et al., DE 2242699 (1973 to Fujisawa), C.A. 78, 134496k (1973); US 3923977 (1975 to Fujisawa). Isoln and characterization of A: H. Aoki et al., J. Antibiot. 29, 492 (1976); of B: M. Kurita et al., ibid. 1243. Nocardicin A has also been produced by Actinosynnema mirum: K. Watanabe et al., ibid. 36, 321 (1983). Structural determination of A and B: M. Hashimoto et al., J. Am. Chem. Soc. 98, 3023 (1976), J. Antibiot. 29, 890 (1976). Isoln, characterization, and structures of C, D, E, F, G: J. Hosoda et al., Agric. Biol. Chem. 41, 2013 (1977). Total synthesis of A: G. A. Koppel et al., J. Am. Chem. Soc. 100, 3933 (1978); W. V. Curran et al., J. Antibiot. 35, 329 (1981); of A and D: T. Kamiya et al., Tetrahedron 1979, 323; of A and B: H. P. Isenring, W. Hofheinz, Tetrahedron 1983, 2591. Biosynthetic studies of A: J. Hosada et al., Agric. Biol. Chem. 41, 2007 (1977); C. A. Townsend et al., J. Am. Chem. Soc. 105, 919 (1983). Series of articles on antimicrobial activity of A: J. Antibiot. 30, 917-944 (1977).
Derivative Type: Nocardicin A
CAS Registry Number: 39391-39-4
CAS Name: (aR,3S)-3-[[(2Z)-[4-[(3R)-3-Amino-3-carboxypropoxy]phenyl](hydroxyimino)acetyl]amino]-a-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic acid
Molecular Formula: C23H24N4O9
Molecular Weight: 500.46
Percent Composition: C 55.20%, H 4.83%, N 11.20%, O 28.77%
Properties: Colorless needles from acidic water, mp 214-216° (dec). [a]D25 -135° (for the sodium salt). uv max (1/15M phosphate buffer): 272 nm (E1%1cm 310); (0.1N NaOH): 244, 283 nm (E1%1cm 460, 270). Sol in alkaline solns, slightly sol in methanol. Insol in chloroform, ethyl acetate, ethyl ether. LD50 in male mice, rats (mg/kg): >8000 orally; >2000 i.v.; 2500, 2600 i.p. (Aoki).
Melting point: mp 214-216° (dec)
Optical Rotation: [a]D25 -135° (for the sodium salt)
Absorption maximum: uv max (1/15M phosphate buffer): 272 nm (E1%1cm 310); (0.1N NaOH): 244, 283 nm (E1%1cm 460, 270)
Toxicity data: LD50 in male mice, rats (mg/kg): >8000 orally; >2000 i.v.; 2500, 2600 i.p. (Aoki)
Derivative Type: Nocardicin B
CAS Registry Number: 60134-71-6
Properties: The E-isomer of nocardicin A. Colorless needles, mp 262-264° (dec). [a]D25 -162° (for the sodium salt). uv max (ethanol/water): 224, 270 nm (e 24600, 9700); (ethanol/0.1N NaOH): 245, 280 nm (e 26000, 11100).
Melting point: mp 262-264° (dec)
Optical Rotation: [a]D25 -162° (for the sodium salt)
Absorption maximum: uv max (ethanol/water): 224, 270 nm (e 24600, 9700); (ethanol/0.1N NaOH): 245, 280 nm (e 26000, 11100)
|