دورية أكاديمية
Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH2 tetrapeptide on crown ether‐based chiral stationary phase.
| العنوان: | Chiral recognition mechanism studies of Tyr‐Arg‐Phe‐Lys‐NH |
|---|---|
| المؤلفون: | Upmanis, Toms, Sevostjanovs, Eduards, Kažoka, Helena |
| المصدر: | Chirality; Jan2024, Vol. 36 Issue 1, p1-19, 19p |
| مصطلحات موضوعية: | CHIRAL stationary phases, CHIRAL recognition, CROWN ethers, AMINO acid residues, PERCHLORIC acid, MASS spectrometry |
| 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‐NH2 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‐NH2 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. [ABSTRACT FROM AUTHOR] |
| Copyright of Chirality is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| قاعدة البيانات: | Complementary Index |
Full Text Finder كن أول من يترك تعليقا!