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Optical resolution HPLC column packings carrying penicillin sulfoxide nucleus. Part IV. Effect of substituents in the benzyl ester group on the optical resolution efficiency

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Summary

Fourteen new vinyl polymers carrying penicillin sulfoxide nucleus, poly (substituted-benzyl 1-oxo-6-metha-crylaminopenicillanate)s, were synthesized in order to investigate the influence of the substituents on the optical resolution capabilities. The resolution efficiency of the high-performance liquid chromatography columns comprising the obtained polymers were examined usingtrans-stilbene oxide and N-acetyl-1-phenethyl-amine. It was found that some columns resolved both racemates, some one, while the others did not separate either. A polymer which has 2,6-dichlorobenzyl moiety was found to resolve both racemates more effectively than the unsubstituted polymer.

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References

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    Y. Saotome, T. Miyazawa, T. Endo, Chromatographia28, 505 (1989), part III.

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    Y. Saotome, T. Miyazawa, T. Endo, Chromatographia28, 509 (1989), part I.

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    Y. Saotome, T. Miyazawa, T. Endo, Chromatographia,28, 511 (1989), part II.

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    Y. Saotome, T. Miyazawa, T. Endo, J. Polym. Sci. Part C, Polym. Lett.26, 485 (1988).

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    Y. Saotome, T. Miyazawa, T. Endo, unpublished. Correspond with Y.S. for synthetic schemes and spectral data for the monomers and their intermediates.

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Saotome, Y., Miyazawa, T. & Endo, T. Optical resolution HPLC column packings carrying penicillin sulfoxide nucleus. Part IV. Effect of substituents in the benzyl ester group on the optical resolution efficiency. Chromatographia 28, 513–515 (1989). https://doi.org/10.1007/BF02261073

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Key Words

  • Column liquid chromatography
  • Optical resolution
  • Polymeric adsorbents
  • Penicillin sulfoxide
  • Substituent effect