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Stereoselective interactions of chiral dipeptides on amylose based chiral stationary phases

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Abstract

Dipeptides are stereo-specifically involved in several biological functions that are challenging to separate enantiomerically. Elution order of enantiomers is an important issue in chiral chromatography. Amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase (CSP) is the best and most-widely-used CSP in chiral separations, but experimental data of enantiomeric separation of dipeptides on this CSP is lacking. Simulation studies were conducted to determine the order of elution and the chiral recognition mechanism of didpetides on this CSP. Results indicated that the docking energy of SR-enantiomers were higher than SS-antipodes. The range of docking energies for SR-enantiomers was −7.44 to −5.92 kcal/mol with CSP, but −7.15 to −5.87 kcal/mol for SS-stereoisomers. Therefore it is predicted that SS-enantiomer will elute first, followed by SR-antipode. Furthermore, hydrogen bondings, van der Waal’s interactions and electrostatic interactions were observed among SR- and SS-enantiomers and chiral grooves of CSP. The number of hydrogen bonds was one in each enantiomer binding except S-Ala-R-Tyr, which contained two hydrogen bonds. No hydrogen bond was found in S-Ala-R-Trp, S-Leu-S-Trp, and S-Leu-S-Tyr dipeptides bindings. The chiral recognition mechanisms dictate different strengths of stereoselective bindings of the enantiomers on CSP.

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Authors and Affiliations

  1. Department of Chemistry, Jamia Millia Islamia, Central University, New Delhi, 110025, India

    Imran Ali & Ashanul Haque

  2. Department of Chemistry, College of Science, King Saud University, Riyadh, 11451, Saudi Arabia

    Zeid A. Al-Othman & Abdulrahman Al-Warthan

  3. Perm National Research Polytechnic University, Perm, 614013, Russia

    Leonid Asnin

Authors
  1. Imran Ali
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  2. Ashanul Haque
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  3. Zeid A. Al-Othman
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  4. Abdulrahman Al-Warthan
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  5. Leonid Asnin
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Correspondence to Imran Ali.

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Ali, I., Haque, A., Al-Othman, Z.A. et al. Stereoselective interactions of chiral dipeptides on amylose based chiral stationary phases. Sci. China Chem. 58, 519–525 (2015). https://doi.org/10.1007/s11426-014-5239-z

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  • DOI: https://doi.org/10.1007/s11426-014-5239-z

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