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    Preparation of heparin/heparan sulfate oligosaccharides with internal N-unsubstituted glucosamine residues for functional studies.

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    Authors
    Wei, Z
    Deakin, Jon A
    Blaum, B S
    Uhrín, D
    Gallagher, John T
    Lyon, Malcolm
    Affiliation
    Institute of Glycobiochemistry, National Engineering Research Centre of Chemical Fertilizer Catalyst, Fu Zhou University, Fu Zhou 350002, People's Republic of China.
    Issue Date
    2011-12
    
    Metadata
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    Abstract
    The rare N-unsubstituted glucosamine (GlcNH (3)(+)) residues in heparan sulfate (HS) have important biological and pathophysiological roles. However, it is difficult to prepare naturally-occuring, GlcNH(3)(+)-containing oligosaccharides from HS because of their low abundance, as well as the inherent problems in both excising and identifying them. Therefore, the ability to chemically generate a series of structurally-defined oligosaccharides containing GlcNH(3)(+) residues would greatly contribute to investigating their natural role in HS. In this study, a series of heparin/HS oligosaccharides, from dp6 up to dp16 in length that possess internal GlcNH(3)(+) residues were prepared by a combination of chemical modification and heparinase I digestion. Purification and structural analysis of the major species derived from the octa- to dodeca-saccharide size fractions indicated the introduction of between 1 and 3 internal GlcNH(3)(+) residues per oligosaccharide. In addition, a GlcNH(3)(+) residue was selectively introduced into an internal position in a tetrasaccharide species by direct chemical modification. This selectivity has potential as an alternative procedure for preparing internally-modified oligosaccharides of various lengths. The utility of such oligosaccharides was demonstrated by a comparison of the binding of three different tetrasaccharide species containing 0, 1 and 2 free amino groups to the NK1 truncated variant of hepatocyte growth factor/scatter factor.
    Citation
    Preparation of heparin/heparan sulfate oligosaccharides with internal N-unsubstituted glucosamine residues for functional studies. 2011, 28 (8-9):525-35 Glycoconj J
    Journal
    Glycoconjugate Journal
    URI
    http://hdl.handle.net/10541/216183
    DOI
    10.1007/s10719-011-9352-3
    PubMed ID
    21948150
    Type
    Article
    Language
    en
    ISSN
    1573-4986
    ae974a485f413a2113503eed53cd6c53
    10.1007/s10719-011-9352-3
    Scopus Count
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    All Paterson Institute for Cancer Research

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