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Chiral recognition mechanism studies of Tyr-Arg-Phe-Lys-NH 2 tetrapeptide on crown ether-based chiral stationary phase.

التفاصيل البيبلوغرافية
العنوان: Chiral recognition mechanism studies of Tyr-Arg-Phe-Lys-NH 2 tetrapeptide on crown ether-based chiral stationary phase.
المؤلفون: Upmanis T; Latvian Institute of Organic Synthesis, Riga, Latvia., Sevostjanovs E; Latvian Institute of Organic Synthesis, Riga, Latvia., Kažoka H; Latvian Institute of Organic Synthesis, Riga, Latvia.
المصدر: Chirality [Chirality] 2024 Jan; Vol. 36 (1), pp. e23619. Date of Electronic Publication: 2023 Sep 12.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley Country of Publication: United States NLM ID: 8914261 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-636X (Electronic) Linking ISSN: 08990042 NLM ISO Abbreviation: Chirality Subsets: MEDLINE
أسماء مطبوعة: Original Publication: New York, NY : Wiley
مواضيع طبية MeSH: Crown Ethers*/chemistry, Stereoisomerism ; Tyrosine ; Phenylalanine ; Chromatography, High Pressure Liquid/methods
مستخلص: Even though chiral recognition for crown-ether CSPs is generally understood, on a molecular level, exact mechanisms for the resolution are still unclear. Furthermore, short peptide analytes often contain multiple amino moieties capable of binding to the crown ether selector. In order to extend the understanding in chiral recognition mechanisms, polar organic mode separation of Tyr-Arg-Phe-Lys-NH 2 tetrapeptide llll/dddd enantiomers on S- and R-(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 stationary phases was studied with 50-mM perchloric acid in methanol as mobile phase. Deviation from the generally acceptable 1:1 stoichiometry was supported by mass spectroscopy analysis of the formed complexes between tetrapeptide enantiomer and crown ether selectors, which revealed adducts possessing 1:1, 1:2, and 1:3 stoichiometry. Further investigation of complexation induced shifts by NMR indicated on different binding mechanisms between llll/dddd enantiomers of Tyr-Arg-Phe-Lys-NH 2 and crown ether selectors. Enantioselective proton shifts were observed in studied tetrapeptide tyrosine and phenylalanine residues exclusively for llll enantiomer upon binding with S-(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 selector (and dddd enantiomer with R-(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 selector), indicating that these two amino acid residues contribute to chiral recognition. The obtained results were in agreement with the LC data.
(© 2023 Wiley Periodicals LLC.)
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معلومات مُعتمدة: IG-2022-08 Latvian Institute of Organic Synthesis; IG-2021-05 Latvian Institute of Organic Synthesis
فهرسة مساهمة: Keywords: amino acids; chiral recognition; crown ether CSPs; enantioselectivity; tetrapeptide
المشرفين على المادة: 0 ((3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6)
0 (Crown Ethers)
02N30CW3X0 (kyotorphin)
42HK56048U (Tyrosine)
47E5O17Y3R (Phenylalanine)
تواريخ الأحداث: Date Created: 20230913 Date Completed: 20240101 Latest Revision: 20240101
رمز التحديث: 20240102
DOI: 10.1002/chir.23619
PMID: 37700546
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-636X
DOI:10.1002/chir.23619