Study on the Method for Oligosaccharide Synthesis Covering the Structural Diversity of Sialic Acid-Aiming at the Understanding of the Polymorphous Functions at the Molecular Level-

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  • Ando Hiromune
    岐阜大学生命科学総合研究支援センター
  • Ishida Hideharu
    Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University
  • Kiso Makoto
    Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University

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Other Title
  • シアル酸分子多様性を網羅する糖鎖合成法の開拓―シアロ糖鎖多機能性の分子理解を目指して―
  • シアルサン ブンシ タヨウセイ オ モウラ スル トウサ ゴウセイホウ ノ カイタク シアロ トウサ タキノウセイ ノ ブンシ リカイ オ メザシテ
  • Aiming at the Understanding of the Polvmorhhous Functions at the Molecular Level
  • シアロ糖鎖多機能性の分子理解を目指して

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For the purpose of the scrutiny of multi-functions of oligosaccharides at the molecular level, the practical method for the chemical construction is essential. In 1989, we have established the practical method for α-selective sialylation that utilizes nitrile solvent effect to fashion thermodynamically-disfavored equatorial glycoside. Due to the powerful method, we have succeeded in many first syntheses of sialyl oligosaccharide complexes such as sialyl Lewis X, GQ 1 b.<BR>Recently, we have developed highly reactive N-Troc-protected sialyl donor and 1, 5-lactamized sialyl acceptor. N-Troc sialyl donor enabled us to perform high-yielding sialylation, and obtained sialoside could be pivotally derived into various homologues containing Neu 5 Gc, NeuNH2 and 8-O-sulfo-Neu 5 Ac. Further, the synergic coupling with 1, 5-lactamized acceptor produced α(2-4) -and α(2-8) -linked disialic acid sequences in high yields, thereby resulting in the first synthesis of glycan portions of gangliosides HLG-2 and Hp-s 6.

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