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Tytuł:
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Enantioselective retention mechanisms of dipeptides on antibiotic-based chiral stationary phases. II. Effect of the methanol content in the mobile phase.
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Autorzy:
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Asnin LD; Perm National Research Polytechnic University, 29 Komsomolsky Al., Perm 614990, Russia. Electronic address: .
Kopchenova MV; Perm National Research Polytechnic University, 29 Komsomolsky Al., Perm 614990, Russia.
Vozisov SE; Perm National Research Polytechnic University, 29 Komsomolsky Al., Perm 614990, Russia.
Klochkova MA; Perm National Research Polytechnic University, 29 Komsomolsky Al., Perm 614990, Russia.
Klimova YA; Perm National Research Polytechnic University, 29 Komsomolsky Al., Perm 614990, Russia.
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Źródło:
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Journal of chromatography. A [J Chromatogr A] 2020 Aug 30; Vol. 1626, pp. 461371. Date of Electronic Publication: 2020 Jun 26.
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Typ publikacji:
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Journal Article
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Język:
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English
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Imprint Name(s):
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Original Publication: Amsterdam ; New York : Elsevier, 1993-
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MeSH Terms:
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Anti-Bacterial Agents/*chemistry
Chromatography, High Pressure Liquid/*methods
Dipeptides/*chemistry
Methanol/*chemistry
Adsorption ; Hydrophobic and Hydrophilic Interactions ; Stereoisomerism ; Thermodynamics
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Contributed Indexing:
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Keywords: Chiral chromatography; Dipeptides; Macrocyclic antibiotics; Retention mechanisms; Ristocetin A
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Substance Nomenclature:
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0 (Anti-Bacterial Agents)
0 (Dipeptides)
2867-20-1 (alanylalanine)
2883-36-5 (leucylleucine)
8L97V505GU (glycylleucine)
Y4S76JWI15 (Methanol)
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Entry Date(s):
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Date Created: 20200817 Date Completed: 20201006 Latest Revision: 20201006
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Update Code:
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20240105
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DOI:
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10.1016/j.chroma.2020.461371
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PMID:
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32797850
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Effect of mobile phase (water-methanol) composition on the enantioseparation of dipeptides on the chiral stationary phase Chirobiotic R was investigated using Ala-Ala, Leu-Leu, Gly-Leu, and Leu-Gly as case studies. The lipophilicity of dipeptides was found to be an essential factor in the dependence of their retention on the methanol percentage, the retention factor of lipophobic dipeptides increasing monotonously and that of lipophilic dipeptides changing according to an asymmetric U-shaped trajectory as methanol concentration increases. The behavior of enantioselectivity as a function of the methanol content also depends on the lipophilicity of dipeptide. For lipophilic Leu-Leu, the dependence has a dome-like shape, and for more lipophobic dipeptides, Ala-Ala and Gly-Leu, it is an increasing function of the methanol concentration. The importance of solvation equilibria in the bulk liquid and on the surface of the stationary phase for the total retention is discussed from the thermodynamic point of view. Special consideration is given to the adsorption of the water-methanol mixture on the surface of the Chirobiotic R stationary phase.
Competing Interests: Declaration of Competing Interest None.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
