Click
here to close Hello! We notice that
you are using Internet Explorer, which is not supported by Echinobase
and may cause the site to display incorrectly. We suggest using a
current version of Chrome,
FireFox,
or Safari.
Glycobiology
2015 May 01;255:535-47. doi: 10.1093/glycob/cwu184.
Show Gene links
Show Anatomy links
Impact of sulfation pattern on the conformation and dynamics of sulfated fucan oligosaccharides as revealed by NMR and MD.
Queiroz IN
,
Wang X
,
Glushka JN
,
Santos GR
,
Valente AP
,
Prestegard JH
,
Woods RJ
,
Mourão PA
,
Pomin VH
.
???displayArticle.abstract???
Sulfated fucans from sea urchin egg jelly express well-defined chemical structures that vary with species. This species specificity regulates the sperm acrosome reaction, a critical step to assure intra-specific fertilization. In addition, these polysaccharides are involved in other biological activities such as anticoagulation. Although sulfation patterns are relevant to the levels of response in both activities, conformation and dynamics of these glycans are also contributing factors. However, data about these features of sulfated fucans are very rare. To address this, we have employed nuclear magnetic resonance experiments combined with molecular dynamics on structurally defined oligosaccharides derived from two sulfated fucans. The results have indicated that the oligosaccharides are flexible in solution. Ring conformation of their composing units displays just the (1)C4 chair configuration. In a particular octasaccharide, composed of two tetrasaccharide sequences, inter-residual hydrogen bonds play a role to decrease dynamics in these repeating units. Conversely, the linking disaccharide [-3)-α-L-Fucp-2(OSO3(-))-(1-3)-α-L-Fucp-4(OCO3(-))-(1-] located right between the two tetrasaccharide units has amplified motions suggested to be promoted by electrostatic repulsion of sulfates on opposite sides of the central glycosidic bond. This conjunction of information about conformation and dynamics of sulfated fucan oligosaccharides provides new insights to explain how these glycans behave free in solution and influenced by sulfation patterns. It may also serve for future studies concerning structure-function relationship of sulfated fucans, especially those involving sea urchin fertilization and anticoagulation.
Albano,
Isolation, fractionation, and preliminary characterization of a novel class of sulfated glycans from the tunic of Styela plicata (Chordata Tunicata).
1986, Pubmed
Albano,
Isolation, fractionation, and preliminary characterization of a novel class of sulfated glycans from the tunic of Styela plicata (Chordata Tunicata).
1986,
Pubmed
Alves,
Females of the sea urchin Strongylocentrotus purpuratus differ in the structures of their egg jelly sulfated fucans.
1998,
Pubmed
,
Echinobase
Alves,
Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins.
1997,
Pubmed
,
Echinobase
Becker,
Conformation of sulfated galactan and sulfated fucan in aqueous solutions: implications to their anticoagulant activities.
2007,
Pubmed
Biermann,
Carbohydrate-based species recognition in sea urchin fertilization: another avenue for speciation?
2004,
Pubmed
,
Echinobase
Cinelli,
Expression of two different sulfated fucans by females of Lytechinus variegatus may regulate the seasonal variation in the fertilization of the sea urchin.
2007,
Pubmed
,
Echinobase
Farndale,
Improved quantitation and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue.
1986,
Pubmed
Foley,
Carbohydrate force fields.
2012,
Pubmed
Glauser,
Structure and haemostatic effects of generic versions of enoxaparin available for clinical use in Brazil: similarity to the original drug.
2012,
Pubmed
Götz,
Routine Microsecond Molecular Dynamics Simulations with AMBER on GPUs. 1. Generalized Born.
2012,
Pubmed
Kirschner,
Solvent interactions determine carbohydrate conformation.
2001,
Pubmed
Kirschner,
GLYCAM06: a generalizable biomolecular force field. Carbohydrates.
2008,
Pubmed
Mourão,
A carbohydrate-based mechanism of species recognition in sea urchin fertilization.
2007,
Pubmed
,
Echinobase
Mulloy,
Sulfated fucans from echinoderms have a regular tetrasaccharide repeating unit defined by specific patterns of sulfation at the 0-2 and 0-4 positions.
1994,
Pubmed
,
Echinobase
Mulloy,
Conformation and dynamics of heparin and heparan sulfate.
2000,
Pubmed
Nivedha,
Importance of ligand conformational energies in carbohydrate docking: Sorting the wheat from the chaff.
2014,
Pubmed
Pomin,
Selective cleavage and anticoagulant activity of a sulfated fucan: stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor II-dependent anticoagulant activity.
2005,
Pubmed
,
Echinobase
Pomin,
Specific sulfation and glycosylation-a structural combination for the anticoagulation of marine carbohydrates.
2014,
Pubmed
,
Echinobase
Pomin,
Mild acid hydrolysis of sulfated fucans: a selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides.
2005,
Pubmed
,
Echinobase
Pomin,
Structure, biology, evolution, and medical importance of sulfated fucans and galactans.
2008,
Pubmed
,
Echinobase
Pomin,
Structure-function relationship of anticoagulant and antithrombotic well-defined sulfated polysaccharides from marine invertebrates.
2012,
Pubmed
Pomin,
Characterization of glycosaminoglycans by 15N NMR spectroscopy and in vivo isotopic labeling.
2010,
Pubmed
Pomin,
Fucanomics and galactanomics: current status in drug discovery, mechanisms of action and role of the well-defined structures.
2012,
Pubmed
Pomin,
Anticoagulant motifs of marine sulfated glycans.
2014,
Pubmed
Pomin,
Review: an overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures.
2009,
Pubmed
,
Echinobase
Pomin,
Solution NMR conformation of glycosaminoglycans.
2014,
Pubmed
Vilela-Silva,
The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization.
2008,
Pubmed
,
Echinobase
Vilela-Silva,
Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus droebachiensis and Strongylocentrotus pallidus ensure species-specific fertilization.
2002,
Pubmed
,
Echinobase
Vilela-Silva,
Structure of the sulfated alpha-L-fucan from the egg jelly coat of the sea urchin Strongylocentrotus franciscanus: patterns of preferential 2-O- and 4-O-sulfation determine sperm cell recognition.
1999,
Pubmed
,
Echinobase
Zsiska,
Influence of sulfate and carboxylate groups on the conformation of chondroitin sulfate related disaccharides.
1993,
Pubmed
