Application of cross‐linked β‐cyclodextrin polymer for adsorption of aromatic amino acids

β‐Cyclodextrin (β‐CyD) was cross‐linked by hexamethylene diisocyanate and the polymer was investigated for adsorption of aromatic amino acids (AAA) from phosphate buffer. High adsorption rates were observed at the beginning and the adsorption equilibrium was then gradually achieved in about 45 min. The adsorption of AAA decreased with the increase of initial concentration and also temperature. Under the same conditions, the adsorption efficiencies of AAA were in the order of L‐tryptophan (L‐Trp) > L‐phenylalanine (L‐Phe) > L‐tyrosine (L‐Tyr). Much higher adsorption values, up to 52.4 and 43.0 mg/g for L‐Trp and L‐Phe, respectively, at 50 mmol/L and 3.2 mg/g for L‐Tyr at 2 mmol/L, were obtained with the β‐CyD polymer at 37 °C. It was shown that the adsorption of AAA on the β‐CyD polymer was consistent with the Freundlich isotherm equation. The adsorption of mixed aromatic amino acids and branched‐chain amino acids (BCAA) showed that AAA were preferentially adsorbed with adsorption efficiencies 10–24%, while those of BCAA were lower than 2%. It seems that the structure and hydrophobicity of amino acid molecules are responsible for the difference in adsorption, by influencing the strength of interactions between amino acid molecule and the polymer. Copyright © 2005 John Wiley & Sons, Ltd.

[1]  M. Komiyama,et al.  Efficient Separation of Hydrophobic Molecules by Molecularly Imprinted Cyclodextrin Polymers , 2004 .

[2]  H. Zou,et al.  Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[3]  H. Zou,et al.  [Cross-linked beta-cyclodextrin polymer used for bilirubin removal]. , 2004, Se pu = Chinese journal of chromatography.

[4]  H. Zou,et al.  Molecularly imprinted monolithic stationary phases for liquid chromatographic separation of enantiomers and diastereomers. , 2003, Journal of chromatography. A.

[5]  T. Akiyama,et al.  Molecular Imprinting of Cyclodextrins Leading to Synthetic Antibodies , 2002 .

[6]  T. Akiyama,et al.  Molecular Imprinting of Cyclodextrin on Silica-Gel Support for the Stationary Phase of High-Performance-Liquid-Chromatography , 2001 .

[7]  R. Breslow,et al.  Synthesis and Binding Properties of Cyclodextrin Trimers. , 2001 .

[8]  T. Akiyama,et al.  Molecular imprinting of cyclodextrin in water for the recognition of nanometer-scaled guests , 2001 .

[9]  R. Bittman,et al.  Hydrophilic cholesterol-binding molecular imprinted polymers , 2001 .

[10]  F. Rigas,et al.  Removal of amino acids from water by adsorption on polystyrene resins , 2001 .

[11]  M. Goto,et al.  Surface imprinted polymers recognizing amino acid chirality , 2000 .

[12]  M. Goto,et al.  Chiral-recognition polymer prepared by surface molecular imprinting technique , 2000 .

[13]  M. Komiyama,et al.  Molecular Imprinting of Cyclodextrin in Water for the Recognition of Peptides , 1999 .

[14]  M. Komiyama,et al.  Molecularly Imprinted Cyclodextrins as Selective Receptors for Steroids1 , 1999 .

[15]  I. Nicholls,et al.  Combined Hydrophobic and Electrostatic Interaction-Based Recognition in Molecularly Imprinted Polymers , 1999 .

[16]  I. Nicholls,et al.  The rational use of hydrophobic effect‐based recognition in molecularly imprinted polymers , 1998, Journal of molecular recognition : JMR.

[17]  K. Sreenivasan.  Synthesis and evaluation of a beta cyclodextrin-based molecularly imprinted copolymer , 1998 .

[18]  M. Komiyama,et al.  Synthesis of molecularly imprinted polymer of βcyclodextrin for the efficient recognition of cholesterol , 1998 .

[19]  A. Rodrigues,et al.  Adsorption of phenylalanine onto polymeric resins: equilibrium, kinetics and operation of a parametric pumping unit , 1998 .

[20]  Frances H. Arnold,et al.  Molecularly imprinted ligand-exchange adsorbents for the chiral separation of underivatized amino acids , 1997 .

[21]  P. Andrew Karplus,et al.  Hydrophobicity regained: Hydrophobicity regained , 1997 .

[22]  H. Asanuma,et al.  Molecularly imprinted polymer of β-cyclodextrin for the efficient recognition of cholesterol , 1997 .

[23]  I. Nicholls,et al.  Molecular Imprinting. Recent innovations in synthetic polymer receptor and enzyme mimics , 1997 .

[24]  P. Karplus,et al.  Hydrophobicity regained. , 1997, Protein science : a publication of the Protein Society.

[25]  G. Carta,et al.  Adsorption of amino acids on porous polymeric adsorbents—I. Equilibrium , 1996 .

[26]  G. Carta,et al.  Adsorption of amino acids on porous polymeric adsorbents—II. Intraparticle mass transfer , 1996 .

[27]  Ronald Breslow,et al.  Molecular recognition by cyclodextrin dimers , 1995 .

[28]  G. Gerber,et al.  Amino acid analysis by dinitrophenylation and reverse-phase high-pressure liquid chromatography. , 1988, Analytical biochemistry.

[29]  K. Wilson,et al.  Amino Acid analyses by high-performance liquid chromatography , 1982 .

[30]  J. Chang,et al.  Amino acid analysis at the picomole level. Application to the C-terminal sequence analysis of polypeptides. , 1981, The Biochemical journal.

[31]  S. Pääbo,et al.  Amino Acid Analysis and Enzymatic Sequence Determination of Peptides by an Improved o-Phthaldialdehyde Precolumn Labeling Procedure , 1981 .

[32]  P. E. Hare,et al.  O-phthalaldehyde: fluorogenic detection of primary amines in the picomole range. Comparison with fluorescamine and ninhydrin. , 1975, Proceedings of the National Academy of Sciences of the United States of America.

[33]  R. C. Weast.  CRC Handbook of Chemistry and Physics , 1973 .

[34]  A. Zamyatnin,et al.  Protein volume in solution. , 1972, Progress in biophysics and molecular biology.