EurekaMag.com logo
+ Site Statistics
References:
53,869,633
Abstracts:
29,686,251
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

Structure-enantioselectivity relationships for the study of chiral recognition in peptide enantiomer separation on cinchona alkaloid-based chiral stationary phases by HPLC: Influence of the N-terminal protecting group



Structure-enantioselectivity relationships for the study of chiral recognition in peptide enantiomer separation on cinchona alkaloid-based chiral stationary phases by HPLC: Influence of the N-terminal protecting group



Journal of Separation Science 26(17): 1499-1508, November



Eleven different N-terminal protecting groups (acetyl, benzoyl, FMOC, etc.) were employed for the HPLC separation of oligoalanine peptide enantiomers containing up to six amino acids. Isocratic HPLC separations were performed using a hydro-organic buffered mobile phase and 4 mm ID columns containing three different chiral anion exchange stationary phases based on cinchona alkaloid-derived chiral selectors. For most peptides successful separations could be obtained with all protecting groups, although those comprising aromatic moieties were found to yield higher enantioselectivities than those with aliphatic residues, since they are capable of undergoing favourable pi-pi interactions with the selector. Systematic investigations concerning the presence or absence of structural features of related protecting groups showed that the use of protecting groups that are optimally adjusted to the binding pocket of the chiral selector effects a significant gain in enantioselectivity. At the same time these studies provided new insights into the chiral recognition mechanism.

(PDF emailed within 0-6 h: $19.90)

Accession: 012592150

Download citation: RISBibTeXText

DOI: 10.1002/jssc.200301577



Related references

Increments to chiral recognition facilitating enantiomer separations of chiral acids, bases, and ampholytes using Cinchona-based zwitterion exchanger chiral stationary phases. Journal of Separation Science 35(13): 1560-1572, 2012

Versatility of cinchona-based zwitterionic chiral stationary phases: enantiomer and diastereomer separations of non-protected oligopeptides utilizing a multi-modal chiral recognition mechanism. Journal of Chromatography. A 1269: 297-307, 2013

Macroporous monolithic chiral stationary phases for capillary electrochromatography: New chiral monomer derived from cinchona alkaloid with enhanced enantioselectivity. Electrophoresis 24(17): 2986-2999, 2003

Study of the enantiomeric separation of the anticholinergic drugs on two immobilized polysaccharide-based chiral stationary phases by HPLC and the possible chiral recognition mechanisms. Electrophoresis, 2018

Structural and temperature effects on enantiomer separations of bicyclo[2.2.2]octane-based 3-amino-2-carboxylic acids on cinchona alkaloid-based zwitterionic chiral stationary phases. Journal of Pharmaceutical and Biomedical Analysis 98: 130-139, 2015

Effects of N-methylation and amidination of cyclic β-amino acids on enantioselectivity and retention characteristics using Cinchona alkaloid- and sulfonic acid-based chiral zwitterionic stationary phases. Journal of Chromatography. A, 2018

Separation of enantiomers on HPLC chiral stationary phases based on human plasma alpha1-acid glycoprotein: effect of sugar moiety on chiral recognition ability. Enantiomer 5(1): 37-45, 2000

Investigation of the structure-selectivity relationships and van't Hoff analysis of chromatographic stereoisomer separations of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on Cinchona alkaloid-based chiral stationary phases. Journal of Chromatography. A 1384: 67-75, 2015

Enantioselective separation of cyclic chiral ketones and their corresponding diastereomeric alcohols by HPLC on chiral and chiral/chiral coupled stationary phases. Chirality 8(8): 551-555, 1996

Enantiomer separation of fungicidal triazolyl alcohols by normal phase HPLC on polysaccharide-based chiral stationary phases. Chirality 11(3): 195-200, 1999

Enantiomer separation by hplc with some novel chiral stationary phases. Journal of Pharmaceutical Sciences 76(11): S9, 1987

Liquid chromatographic enantiomer separation and chiral recognition by cinchona alkaloid-derived enantioselective separation materials. Advances in Chromatography 46: 1-107, 2008

A combinatorial approach to chiral recognition Preparation of chiral stationary phases containing beta-lactam selectors for the HPLC separation of enantiomers. Abstracts of Papers American Chemical Society 224(1-2): ORGN 432, 2002

HPLC with carbohydrate carbamate chiral phases Influence of chiral phase structure on enantioselectivity. Chirality 6(2): 135-140, 1994

Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds. Journal of Pharmaceutical and Biomedical Analysis 124: 164-173, 2016