Iron(II)-Assisted Assembly of Trivalent GalNAc Clusters and Their Interactions with GalNAc-Specific Lectins.

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著者

    • Sakai Shin
    • Department of Materials Science, Faculty of Engineering, Tottori University

抄録

A novel metal-assisted assembly of mulitivalent carbohydrate ligands is described. A bipyridine-modified <i>N</i>-acetylgalactosamine (bipy-GalNAc) undergoes Fe(II)-induced self-association to form a trimeric GalNAc ligand (Fe<sup>II</sup>(bipy-GalNAc)<sub>3</sub>). The synthetic GalNAc cluster strongly binds to <i>Vicia villosa</i> B<sub>4</sub> lectin and <i>Glycin Max</i> lectin, which recognizes multiple GalNAc residues. The trimeric GalNAc ligand is formed as a mixture of four diastereomeric isomers: <i>Δ</i>-<i>fac</i>, <i>Λ</i>-<i>fac</i>, <i>Δ</i>-<i>mer</i>, and <i>Λ</i>-<i>mer</i>. These stereoisomers are in a dynamic equilibrium at room temperature. The equilibrium allows the spatial arrangement of the three GalNAc residues to change in order to fit into a multivalent carbohydrate binding site of the lectins. Detailed analysis of the kinetic and thermodynamic data for the isomerization can provide structural information of the carbohydrate binding site of the lectins.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 72(6), 1313-1319, 1999

    公益社団法人 日本化学会

各種コード

  • NII論文ID(NAID)
    130004150385
  • 本文言語コード
    ENG
  • ISSN
    0009-2673
  • データ提供元
    J-STAGE 
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