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Scalemic and racemic imprinting with a chiral crosslinker.
Hebert, Britney; Meador, Danielle S; Spivak, David A.
Afiliação
  • Hebert B; Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
  • Meador DS; Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
  • Spivak DA; Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA. Electronic address: david_spivak@chem.lsu.edu.
Anal Chim Acta ; 890: 157-64, 2015 Aug 26.
Article em En | MEDLINE | ID: mdl-26347178
ABSTRACT
The development of molecularly imprinted chiral stationary phases has traditionally been limited by the need for a chiral pure template. Paradoxically, availability of a chiral pure template largely defeats the purpose of developing a chiral stationary phase. To solve this paradox, imprinting of scalemic and racemic template mixtures was investigated using both chiral (N-α-bismethacryloyl-L-alanine) and achiral (N,O-bisacrylamide ethanolamine) crosslinkers. Imprinting of scalemic mixtures provided polymers capable of partial separation of Boc-tyrosine enantiomers with virtually the same results when using either the chiral or achiral crosslinker. However, the chiral crosslinker was required for chiral differentiation by the racemic imprinted polymers which were evaluated in both batch rebinding and chromatographic modes. Batch rebinding analysis revealed intersecting binding isotherms for the L- and D-Boc-tyrosine, indicating bias for the D or L enantiomer is concentration dependent. Partial chromatographic separation was achieved by the racemic imprinted polymers providing variable D or L bias in equal probability over multiple replicates of polymer synthesis. Correlation of enantiomer bias with the batch rebinding results and optimization of HPLC parameters are discussed.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2015 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2015 Tipo de documento: Article