Preparation of heparin/heparan sulfate oligosaccharides with internal N-unsubstituted glucosamine residues for functional studies.
AffiliationInstitute of Glycobiochemistry, National Engineering Research Centre of Chemical Fertilizer Catalyst, Fu Zhou University, Fu Zhou 350002, People's Republic of China.
MetadataShow full item record
AbstractThe 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.
CitationPreparation of heparin/heparan sulfate oligosaccharides with internal N-unsubstituted glucosamine residues for functional studies. 2011, 28 (8-9):525-35 Glycoconj J
- A new sequencing approach for N-unsubstituted heparin/heparan sulfate oligosaccharides.
- Authors: Liang QT, Xiao XM, Lin JH, Wei Z
- Issue date: 2015 Jul
- Preparation and characterization of heparin hexasaccharide library with N-unsubstituted glucosamine residues.
- Authors: Liang QT, Du JY, Fu Q, Lin JH, Wei Z
- Issue date: 2015 Nov
- Distinct substrate specificities of bacterial heparinases against N-unsubstituted glucosamine residues in heparan sulfate.
- Authors: Wei Z, Lyon M, Gallagher JT
- Issue date: 2005 Apr 22
- Location of N-unsubstituted glucosamine residues in heparan sulfate.
- Authors: Westling C, Lindahl U
- Issue date: 2002 Dec 20
- Production of size-defined heparosan, heparan sulfate, and heparin oligosaccharides by enzymatic depolymerization.
- Authors: Brown S, Kuberan B
- Issue date: 2015