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Syntheses of α-dystroglycan derived glycosyl amino acids carrying a novel mannosyl serine/threonine linkage

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Abstract

α-Dystroglycan (α-DG) is a membrane-associated, extracellular glycoprotein. It is anchored to the cell-membrane by binding to the transmembrane glycoprotein β-dystroglycan (β-DG) to form an α/β-DG-complex. It was discovered that the bovine peripheral nerve α-DG possesses the Ser/Thr linked tetrasaccharide as the major constituent of the O-linked carbohydrates, which was proposed to contribute laminin binding activity of this glycoprotein.

This structure has a striking feature in terms of the mode of linkage between oligosaccharide and the core protein. It has a mannose residue linked to the core protein through Ser/Thr residue. A similar structure was proposed to exist in brain derived HNK-1 immunoreactive O-glycans. Being interested in the structural novelty and potential biological significance of this type of glycan chains, the chemical synthesis of Ser/Thr linked mannose containing tetrasaccharide was investigated. Tetrasaccharide donor was constructed from monosaccharide blocks and coupled with Ser/Thr derivatives. Subsequent deprotection afforded target tetraosyl serine. Furthermore, synthetic routes to lower homologues, namely Gal-β-(1,4)-GlcNAc-β-(1,2)-Man-α-Ser and GlcNAc-β-(1,2)-Man-α-Ser were also provided.

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Authors and Affiliations

  1. RIKEN (The Institute of Physical and Chemical Research), Hirosawa 2-1, Wako-shi, Saitama, 351-0198, Japan

    Joachim Seifert, Tomoya Ogawa, Sadamu Kurono & Yukishige Ito

Authors
  1. Joachim Seifert
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  2. Tomoya Ogawa
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  3. Sadamu Kurono
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  4. Yukishige Ito
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Seifert, J., Ogawa, T., Kurono, S. et al. Syntheses of α-dystroglycan derived glycosyl amino acids carrying a novel mannosyl serine/threonine linkage. Glycoconj J 17, 407–423 (2000). https://doi.org/10.1023/A:1007112232131

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