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

• Shin Sakai

  Department of Materials Science, Faculty of Engineering, Tottori UniversityKoyama-cho Minami, Tottori 680-8552

• Yoshihiro Shigemasa

  Department of Materials Science, Faculty of Engineering, Tottori UniversityKoyama-cho Minami, Tottori 680-8552

• Tomikazu Sasaki

  Department of Chemistry, BG-10, University of WashingtonSeattle, WA 98195 , USA

抄録

A novel metal-assisted assembly of mulitivalent carbohydrate ligands is described. A bipyridine-modified N-acetylgalactosamine (bipy-GalNAc) undergoes Fe(II)-induced self-association to form a trimeric GalNAc ligand (FeII(bipy-GalNAc)3). The synthetic GalNAc cluster strongly binds to Vicia villosa B4 lectin and Glycin Max lectin, which recognizes multiple GalNAc residues. The trimeric GalNAc ligand is formed as a mixture of four diastereomeric isomers: Δ-fac, Λ-fac, Δ-mer, and Λ-mer. 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, 1999-06-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360283694081277952
• NII論文ID: 130004150385
• DOI: 10.1246/bcsj.72.1313
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/72/6/1313/56199119/bcsj.72.1313.pdf
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