Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research.

Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Research Abstract Details 

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Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Abstract Text:

The total synthesis of 6-O-sulfo-sialylparagloboside is described. A suitably protected beta-d-GlcpNAc-(1-->3)-beta-d-Galp-(1-->4)-d-GlcpOSE derivative was glycosylated with an alpha-d-Neup5Ac-(2-->3)-d-Galp derived imidate to give the corresponding protected alpha-d-Neup5Ac-(2-->3)-beta-d-Galp-(1-->4)-beta-d-GlcpNAc-(1-->3)-beta-d-Galp-(1-->4)-d-GlcpOSE pentasaccharide derivative. Proper manipulation of the protecting groups of the pentasaccharide afforded the corresponding glycosyl imidate, which was coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol. Selective reduction of the azido group, N-acylation with octadecanoic acid, 6-O-sulfation of the GlcpNAc residue, and complete removal of the protecting groups gave the desired 6-O-sulfo-sialylparagloboside.

Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Publishing Authors By Initials

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Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Carbohydrate research

VOLUME: 343

Page Numbers: 1849-57

Journal Abbreviation: Carbohydr. Res.

ISSN: 0008-6215

DAY: 18

MONTH: 03

YEAR: 2008

Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research.

AFFILIATION: Department of Applied Bio-organic Chemistry, Faculty of Applied Biological Sciences, Gifu University, Gifu 501-1193, Japan.

Country: Netherlands

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MEDLINETA: Carbohydr Res

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