Abstract
The epimerization rate constants of R- and S-epimers of moxalactam (LMOX) in a frozen aqueous solution decreased as the temperature decreased. The reaction proceeded in the unfrozen region remaining in the frozen solution, without being affected by the ice. The reaction stopped completely below the collapse temperature of the LMOX aqueous solution. The ratio of R- and S-epimers at equilibrium, which was equal to the ratio of the epimerization rate constant, increased as the temperature decreased. This change in the ratio at equilibrium could be ascribed to the difference in the activation energy between the two epimers.
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REFERENCES
R. Wise, P. J. Wills, and K. A. Bedford. Antimicrob. Agents Chemother. 20:30–32 (1981).
R. Wise, N. Wright, and P. J. Wills. Rev. Infect. Dis. 4(Suppl.):S564–S568 (1982).
R. Konaka, K. Kuruma, R. Nishimura, Y. Kimura, and T. Yoshida. J. Chromatogr. 225:169–178 (1981).
A. R. Butler and T. C. Bruice. J. Am. Chem. Soc. 85:313–319 (1964).
R. E. Pincock and T. E. Kiovsky. J. Am. Chem. Soc. 87:2072–2073 (1965).
R. E. Pincock and T. E. Kiovsky. J. Am. Chem. Soc. 87:4100–4107 (1965).
R. E. Pincock and T. E. Kiovsky. J. Am. Chem. Soc. 88:51–55 (1966).
N. H. Grant, D. E. Clark, and H. E. Alburn. J. Am. Chem. Soc. 83:4476–4477 (1961).
T. C. Bruice and A. R. Butler. J. Am. Chem. Soc. 86:4104–4108 (1964).
N. H. Grant and H. E. Alburn. J. Am. Chem. Soc. 87:4174–4177 (1965).
N. H. Grant and H. E. Alburn. Biochemistry 4:1913–1916 (1965).
W. H. Prusoff. Biochim. Biophys. Acta 68:302–310 (1963).
N. H. Grant and H. E. Alburn. Arch. Biochem. Biophys. 118:292–296 (1967).
M. Narisada and W. Nagata. Shionogi & Co., Ltd., U.S. Patent 4323567 (1982).
M. Inoue, K. Shima, and K. Inazu. Yakugaku Zasshi 104:966–972 (1984).
D. A. Marsh, A. R. Olson, K. A. Regensburger, M. Proefke, W. J. Smith, III, D. Ham, and S. A. Ludwig. Pharm. Res. 3 (5):63S (abstr. 94) (1986).
B. J. Luyet, D. Sager, and P. M. Gehenio. Biodynamica 10:123–132 (1967).
B. J. Luyet. Ann. N.Y. Acad. Sci. 85:549–569 (1960).
N. Hashimoto, T. Tasaki, and H. Tanaka. J. Pharm. Sci. 73:369–373 (1984).
C. M. Metzler, G. L. Elfring, and A. J. McEwen. Biometrics 30:No. 3 (1974).
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Hashimoto, N., Ichihashi, T., Yamamoto, E. et al. Epimerization Kinetics of Moxalactam in Frozen Solution. Pharm Res 5, 266–271 (1988). https://doi.org/10.1023/A:1015918518922
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DOI: https://doi.org/10.1023/A:1015918518922