The facile HPLC enantioresolution of amino acids, peptides on naphthylethylcarbamate-beta-cyclodextrin bonded phases using the acetonitrile-based mobile phase after their pre-column derivatization with phenyl isothiocyanate: factors that affect the resolu

Abstract:

:A variety of alpha-amino acids are enantioresolved for the first time on naphthylethylcarbamate-beta-cyclodextrin bonded phases (i.e., SN- and RN-beta-CD) using the acetonitrile-based mobile phase after their pre-column derivatization with phenyl isothiocyanate in alkaline medium. The resolution is better obtained on RN-beta-CD phase and fails to reproduce if the amino acid is N-benzoylated or N-carbobenzyloxylated under the same chromatographic conditions. The enhanced resolution is believed to be due to the re-location of the hydrogen receptor site from sulfur to nitrogen on the isothiocyanyl fragment of derivatizing reagent, which in turn changes the enantioselectivity. Also, the sulfur atom is larger in size and subject to steric hindrance more significantly in comparison with oxygen. The carboxyl group of amino acid is essential toward a satisfactory resolution. The position of the amino group on the backbone affects the resolution as well. Finally, the resolution is either not observed or unsatisfactory in the reversed- or normal phase mode for most of the amino acids examined in this study.

journal_name

Amino Acids

journal_title

Amino acids

authors

Chen S

doi

10.1007/s00726-003-0038-4

subject

Has Abstract

pub_date

2004-06-01 00:00:00

pages

291-8

issue

3

eissn

0939-4451

issn

1438-2199

journal_volume

26

pub_type

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