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Validated Chiral LC Method for the Enantiomeric Separation of β-Amino-β-(3-Methoxyphenyl) Propionic Acid

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Abstract

A chiral liquid chromatographic method for enantiomeric resolution of β-amino-β-(3-methoxyphenyl) propionic acid was developed and validated. The “hybrid” π-electron donor–acceptor based stationary phase (R,R) Whelk-01 was found to be enantiomerically selective for (R) and (S) enantiomers of β-amino-β-(3-methoxyphenyl) propionic acid with a resolution greater than 2.0. The effects of isopropyl alcohol and ethanol on enantioselectivity and resolution of enantiomers were evaluated. Calibration curves were linear over the range of 0.10–1.00, with a regression coefficient (r) of 0.999. The limit of detection (LOD) and limit of quantification (LOQ) were 300 and 1,000 ng mL−1 respectively for 10 μL injection volume. The percentage RSD of the peak area of six replicate injections of (S) enantiomer at LOQ concentration was 2.8. The percentage recovery of (S) enantiomer from (R) enantiomer samples ranged from 92 to 102. The test solution was observed to be stable up to 24 h after the preparation. The developed normal phase chiral LC method can be used for the enantiomeric purity evaluation of R-β-amino-β-(3-methoxyphenyl) propionic acid.

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Acknowledgements

The authors wish to thank the management of Dr. Reddy’s group for supporting this work (part of Ph. D work). The authors wish to acknowledge the Process Research group for providing the samples to carry out the above work. The authors also like to thank colleagues in Analytical Research of Custom Pharmaceutical Services for their co-operation in carrying out this work.

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Authors and Affiliations

  1. Analytical Research, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories, Hyderabad, 500049, India

    P. Madhavan, Bandlamudi Mallikarjuna Rao, B. Pravin & S. Abhishek

  2. Process Research, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories, Hyderabad, 500049, India

    P. R. Kumar & M. Sreenivasulu

  3. Department of Chemistry, J.N.T.U. College of Engineering, Anantapur, 515002, India

    K. B. Chandrasekhar

Authors
  1. P. Madhavan
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  2. Bandlamudi Mallikarjuna Rao
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  3. B. Pravin
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  4. S. Abhishek
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  5. P. R. Kumar
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  6. M. Sreenivasulu
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  7. K. B. Chandrasekhar
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Corresponding author

Correspondence to Bandlamudi Mallikarjuna Rao.

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Madhavan, P., Rao, B.M., Pravin, B. et al. Validated Chiral LC Method for the Enantiomeric Separation of β-Amino-β-(3-Methoxyphenyl) Propionic Acid. Chroma 66, 243–246 (2007). https://doi.org/10.1365/s10337-007-0284-9

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  • DOI: https://doi.org/10.1365/s10337-007-0284-9

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