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

Christoph Czerwenka, Michael Lämmerhofer, Wolfgang Lindner

Veröffentlichungen: Beitrag in FachzeitschriftArtikelPeer Reviewed

Abstract

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 p-p 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.
OriginalspracheEnglisch
Seiten (von - bis)1499-1508
Seitenumfang10
FachzeitschriftJournal of Separation Science
Jahrgang26
Ausgabenummer17
PublikationsstatusVeröffentlicht - 2003

ÖFOS 2012

  • 1040 Chemie

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