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Novel chiral selectors anchored on polydimethylsiloxane as stationary phases for separation of derivatized amino acid enantiomers by capillary gas chromatography
Author(s) -
Abe Iwao,
Ohtani Susumu
Publication year - 2006
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200500283
Subject(s) - enantiomer , chemistry , racemization , chromatography , polydimethylsiloxane , isopropyl , amino acid , gas chromatography , derivatization , amide , organic chemistry , aspartic acid , high performance liquid chromatography , biochemistry
Six chiral selectors of S ‐(–)‐ t ‐Leu‐cyclopropylamide, S ‐(–)‐ t ‐Leu‐cyclopentylamide, S ‐ (–)‐ t ‐Leu‐cyclohexylamide, S ‐(–)‐ t ‐Leu‐cycloheptylamide, S ‐(–)‐ t ‐Leu‐cyclooctylamide, S ‐(–)‐ t ‐Leu‐cyclododecylamide have been prepared and anchored individually through amide bonding to a polydimethylsiloxane functionalized with 2,2,2‐trifluoroethyl ester groups by way of nucleophilic displacement reaction. The resulting chiral polysiloxanes have been provided as stationary phases for the separation of amino acid enantiomers by capillary GC. Amino acids were derivatized into N(O) ‐trifluoroacetyl isopropyl esters. Especially, polydimethylsiloxane anchored with S ‐(–)‐ t ‐Leu‐cyclooctylamide was found to be efficient for the separation of aspartic acid (Asp) enantiomers. The method was applied to the estimation of ages from the extent of Asp racemization in human dentines.