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


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2000-06

AUTHORS

Joachim Seifert, Tomoya Ogawa, Sadamu Kurono, Yukishige Ito

ABSTRACT

Alpha-dystroglycan (alpha-DG) is a membrane-associated, extracellular glycoprotein. It is anchored to the cell-membrane by binding to the transmembrane glycoprotein beta-dystroglycan (beta-DG) to form an alpha/beta-DG-complex. It was discovered that the bovine peripheral nerve alpha-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-beta-(1,4)-GlcNAc-beta-(1,2)-Man-alpha-Ser and GlcNAc-beta-(1,2)-Man-alpha-Ser were also provided. More... »

PAGES

407-423

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1007112232131

DOI

http://dx.doi.org/10.1023/a:1007112232131

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1051325716

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/11294507


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