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Chiral analysis of β-alanyl-D,L-tyrosine and its derivatives and estimation of binding constants of their complexes with 2-hydroxypropyl-β-cyclodextrin by capillary electrophoresis
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SYSNO ASEP 0557298 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Chiral analysis of β-alanyl-D,L-tyrosine and its derivatives and estimation of binding constants of their complexes with 2-hydroxypropyl-β-cyclodextrin by capillary electrophoresis Author(s) Sázelová, Petra (UOCHB-X) RID, ORCID
Šolínová, Veronika (UOCHB-X) RID, ORCID
Schimperková, Tereza (UOCHB-X)
Jiráček, Jiří (UOCHB-X) RID, ORCID
Kašička, Václav (UOCHB-X) RID, ORCIDSource Title Journal of Separation Science. - : Wiley - ISSN 1615-9306
Roč. 45, č. 17 (2022), s. 3328-3338Number of pages 11 s. Language eng - English Country DE - Germany Keywords binding constant ; capillary electrophoresis ; enantioseparation ; chiral separation ; β-alanyltyrosine ; 2-hydroxypropyl-β-cyclodextrin OECD category Analytical chemistry R&D Projects GA20-03899S GA ČR - Czech Science Foundation (CSF) EF16_019/0000729 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000790115700001 EID SCOPUS 85129563676 DOI 10.1002/jssc.202200158 Annotation Chiral CE methods were developed for the elucidation of L- or D-configuration of tyrosine residue in antimicrobial dipeptide beta-alanyl-tyrosine (beta-Ala-Tyr) isolated from the hemolymph of larvae of fleshfly Neobellieria bullata and for the evaluation of enantiopurity of its synthetic isomers (beta-Ala-D-Tyr and beta-Ala-L-Tyr), and enantiomers of their amidated and acetylated derivatives, beta-Ala-D,L-Tyr-NH2 and N-Ac-beta-Ala-D,L-Tyr, respectively. Baseline separations were achieved for all three pairs of enantiomers: (i) for beta-Ala-D,L-Tyr in acidic background electrolyte composed of 32/50 mM tris(hydroxymethyl)aminomethane/H3PO4, pH 2.5, and 20 mg/mL 2-hydroxypropyl-beta-cyclodextrin as chiral selector, (ii) for beta-Ala-D,L-Tyr-NH, enantiomers in acidic background electrolyte consisting of 48/50 mM tris(hydroxymethyl)aminomethane/H3PO4, pH 3.5, and 30 mg/mL 2-hydroxypropyl-beta-cyclodextrin, and (iii) for enantiomers of N-Ac-beta-Ala-D,L-Tyr in alkaline background electrolyte composed of 50/49 mM Na2B4O7/NaOH, pH 10.5, and 60 mg/mL 2-hydroxypropyl-beta-cyclodextrin. From CE analyses of mixed samples of isolated beta-Ala-Tyr and synthetic standards beta-Ala-L-Tyr and beta-Ala-DTyr, it turned out that isolated beta-Ala-Tyr was pure L-enantiomer. In addition, the average apparent binding constants, K-b, and average actual ionic mobilities of the complexes of beta-Ala-D,L-Tyr and its above derivatives with 2-hydroxypropyl-Acyclodextrin were determined. These complexes were weak, with K-b values ranging from 11.2 to 79.1 L/mol. Their cationic mobilities were equal to (5.6-9.2) x 10(-9) m(2)/V/s, and anionic mobilities to (-1.3-1.6) x 10(-9) m(2)/V/s. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2023 Electronic address https://doi.org/10.1002/jssc.202200158
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