Summary
The presence of the oxygen atom in place of the sulfur atom has significant impact on the polarity of the β-lactam derivative. This has been illustrated by direct comparison of HPLC data of 4 different cephalosporin derivatives and their oxa analogues.
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N. Neuss, R.D. Miller, C.A. Affolder, W. Nakatsukasa, J. Mabe, L.L. Huckstep, N. De La Higuera, A.H. Hunt, J.L. Occolowitz and J.H. Gilliam, Helv. chim. Acta63, 1119 (1980).
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Y. Sendo, T. Konoike, M. Murakami and M. Yoshioka, Heterocycles (1981).
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Acknowledgment. We gratefully acknowledge the cooperation of Drs Yuji Sendo, Toshiro Konoike, Masayuki Murakami and Mitsuru Yoshioka of Shionogi Research Laboratories, Shionogi and Co., Ltd, Fukushima-ku, Osaka, 553, Japan, who synthesized the oxa-β-lactams and made them available for this study.
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Miller, R.D., Affolder, C. & Neuss, N. HPLC of cephalosporins and their oxa-derivatives. Experientia 37, 928–930 (1981). https://doi.org/10.1007/BF01971758
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DOI: https://doi.org/10.1007/BF01971758