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1995 Fiscal Year Final Research Report Summary

Chiral recognition based on a protein-domain-bonded column

Research Project

Project/Area Number 06672159
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Physical pharmacy
Research InstitutionMukogawa Women's University

Principal Investigator

HAGINAKA Jun  Mukogawa Women's Univ., Faculty of Pharm.Sci., Professor, 薬学部, 教授 (20164759)

Project Period (FY) 1994 – 1995
KeywordsOvomucoid / Ovomucoid Domain / Ovoglycoprotein / Chiral recognition / Chiral staionary phases
Research Abstract

Titration of the third domain of turkey and chicken ovomucoid (OMTKY3 and OMCHI3, respectively) with U-80,413, a 2-arylpropionic acid derivative, in conjunction with NMR measurements enabled the identification of the amino acids responsible for binding. Molecular modeling of the ligand-protein complexation provided insights into ability of a protein surface to discriminate the U-80,413 enantiomers on the basis of multiple intermolecular interactions. We found that similarities and differences in orientation and intermolecular interactions between the R- and S-enantiomers of U-80,413. The carboxyl groups of each enantiomer engage in electrostatic interactions with positive charge on Arg 21. The carbonyl group on U-80,413's central ring shares a hydrogen bond with NH_3^+ group of Lys 34. The distinguishing difference between enantiomers is the proximity of the phenylgroup of R-enantiomer and Phe 53.
Commercial chicken ovomucoid (OMCHI) and isolated OMCHI by precipitation with organic solvents from egg whites, which are crude, were fractionated by anion- and cation-exchange chromatography. The obtained four fractions were characterized by reversed-phase chromatography, N-terminal sequencing, matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, determination of sugar contents and trypsin-inhibitory activities. Three fractions were OMCHI variants differing in carbohydrate composition, especially in sialic acid content, and the other fraction was tentatively termed ovoglycoprotein (OGCHI). These OMCHI variants and OGCHI were bound to aminopropyl-silica gels to evaluate chiral recognition ability. However, neither OMCHI variant gave appreciable chiral recognition ability, while the OGCHI gave much more excellent chiral recognition properties than those of the OMCHI reported previously. This reveals that chiral recognition ability of the OMCHI reported previoulsy comes from the OGCHI,which is present in crude OMCHI as an impurity.

  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Jun Haginaka: "Retention and enantioselective properties of ovomucoid-bonded silica columns. Influence of physical property of base materials and spacer length." J. Chromatogr. A. 660. 275-281 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Separation of enantiomers on a lysozyme-bonded silica column" J. Chromatogr. A. 666. 203-210 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Retention and enantioselectivity of 2-arylpropionic acid derivatives on an avidin-bonded silica column. Influence of base materials,spacer length and modification" J. Chromatogr. A. 677. 229-237 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Enantioselectivity of bovin serum albumin-bonded columns produced with isolated protein fragments" J. Chromatogr. A. 694. 71-80 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Retentive and enantioselective properties of ovmucoid-bonded silica columns. Influence of protein purity and isolation method" J. Chromatogr. A. 704. 279-287 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Separation of enantiomers on a pepsin-bonded column" J. Chromatogr. A. 708. 161-168 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Thomas C. Pinkerton: "Protein-binding chiral descrimination of HPLC stationary phases made with whole,fragmented and third domain turkey ovomucoid" Anal. Chem.67. 2354-2367 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Absence of chiral recognition ability in ovomucoid : Ovoglycoprotein-bonded HPLC stationary phases for chiral recognition" Anal. Chem.67. 2539-2547 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun Haginaka: "Retention and enantioselective properties of ovomucoid-bonded silica columns. Influence of physical property of base materials and spacer length" J.Chromatogr.A.660. 275-281 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Separation of enantiomers on a lysozyme-bonded silica column" J.Chromatogr.A. 666. 203-210 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Retention and enantioselectivity of 2-arylpropionic acid derivatives on an avidin-bonded silica column. Influence of base materials, spacer length and modification" J.Chromatogr.A. 677. 299-237 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Enantioselectivity of bovin serum albumin-bonded columns produced with isolated protein fragments" J.Chromatogr.A. 694. 71-80 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Retentive and enantioselective properties of ovmucoid-bonded silica columns. Influence of protein purity and isolation method" J.Chromatogr.A. 704. 279-287 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Separation of enantiomers on a pepsin-bonded column" J.Chromatogr.A. 708. 161-168 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Thomas C.Pinkerton: "Protein-binding chiral descrimination of HPLC staionary phases made with whole, fragmented and third domain turkey ovomucoid" Anal.Chem.67. 2354-2367 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Jun Haginaka: "Absence of chiral recognition ability in ovomucoid : Ovoglycoprotein-bonded HPLC stationary phases for chiral recognition" Anal.Chem.67. 2539-2547 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1997-03-04  

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