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Stereomeric resolution and modeling of DL-alanine-DL-phenyl alanine dipeptide on amycoat-RP column

Abstract

Stereomeric resolution and docking studies of four stereomers of DL-alanine-DL-phenyl alanine dipeptide were performed with AmyCoat-RP column. The eluent used was methanol:ammonium acetate (10 mM):formic acid (70:30:0.05, v/v) with 0.8 mL/min flow rate, detection at 275 nm and 27 ± 2 ºC temperature. The values of retention factors for LL-, DD-, DL- and LD- stereomers were 1.36, 2.21, 8.63 and 11.3. The values of separation factors were 1.63, 3.91 and 1.31. The values of resolution factors were 1.70, 6.43 and 2.14, respectively. The detections and quantitation limits were 0.62-1.43 and 3.10-10.0 ng. The docking studies proven the order of elution and the stereomeric mechanism. The different forces responsible for stereomeric resolution were hydrogen bondings, hydrophobic interactions, π-π forces, van der Waal’s attractions and steric effect. The described stereomeric resolution of the reported racemic dipeptide is highly useful. It may be used to access the quantities of various stereomeric in any unknown matrices.

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Publication details

The article was received on 15 Oct 2019, accepted on 14 Nov 2019 and first published on 18 Nov 2019


Article type: Paper
DOI: 10.1039/C9AY02226K
Anal. Methods, 2019, Accepted Manuscript

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    Stereomeric resolution and modeling of DL-alanine-DL-phenyl alanine dipeptide on amycoat-RP column

    N. H. Al-Shaalan, I. Ali, Z. A. Al Othman, L. H. Al-Wahaibi and H. Alabdulmonem, Anal. Methods, 2019, Accepted Manuscript , DOI: 10.1039/C9AY02226K

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