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A unique 2-sulfated {beta}-galactan from the egg jelly of the sea urchin Glyptocidaris crenularis: conformation flexibility versus induction of the spermacrosome reaction.
Castro MO
,
Pomin VH
,
Santos LL
,
Vilela-Silva AC
,
Hirohashi N
,
Pol-Fachin L
,
Verli H
,
Mourão PA
.
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Sulfated polysaccharides from the egg jelly of sea urchins act as species-specific inducers of the sperm acrosome reaction, which is a rare molecular mechanism of carbohydrate-induced signal-transduction event in animal cells. The sea urchin polysaccharides differ in monosaccharide composition (l-fucose or l-galactose), glycosylation, and sulfation sites, but they are always in the alpha-anomeric configuration. Herein, structural analysis of the polysaccharide from the sea urchin Glyptocidaris crenularis surprisingly revealed a unique sulfated beta-d-galactan composed by (3-beta-d-Galp-2(OSO(3))-1-->3-beta-d-Galp-1)(n) repeating units. Subsequently, we used the G. crenularis galactan to compare different 2-sulfated polysaccharides as inducers of the acrosome reaction using homologous and heterologous sperm. We also tested the effect of chemically over-sulfated galactans. Intriguingly, the anomeric configuration of the glycosidic linkage rather than the monosaccharide composition (galactose or fucose) is the preferential structural requirement for the effect of these polysaccharides on sea urchin fertilization. Nuclear magnetic resonance and molecular dynamics indicate that sulfated alpha-galactan or alpha-fucan have less dynamic structural behavior, exhibiting fewer conformational populations, with an almost exclusive conformational state with glycosidic dihedral angles Phi/Psi = -102 degrees /131 degrees . The preponderant conformer observed in the sulfated alpha-galactan or alpha-fucan is not observed among populations in the beta-form despite its more flexible structure in solution. Possibly, a proper spatial arrangement is required for interaction of the sea urchin-sulfated polysaccharides with the specific sperm receptor.
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
Amornrut,
A new sulfated beta-galactan from clams with anti-HIV activity.
1999,
Pubmed
Becker,
Conformation of sulfated galactan and sulfated fucan in aqueous solutions: implications to their anticoagulant activities.
2007,
Pubmed
Becker,
Molecular dynamics and atomic charge calculations in the study of heparin conformation in aqueous solution.
2005,
Pubmed
Biermann,
Carbohydrate-based species recognition in sea urchin fertilization: another avenue for speciation?
2004,
Pubmed
,
Echinobase
Bilan,
Structure of a highly pyruvylated galactan sulfate from the Pacific green alga Codium yezoense (Bryopsidales, Chlorophyta).
2007,
Pubmed
Farias,
A preponderantly 4-sulfated, 3-linked galactan from the green alga Codium isthmocladum.
2008,
Pubmed
Farndale,
Improved quantitation and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue.
1986,
Pubmed
Gerwig,
Determination of the absolute configuration of mono-saccharides in complex carbohydrates by capillary G.L.C.
1979,
Pubmed
Hirohashi,
Egg fucose sulfate polymer, sialoglycan, and speract all trigger the sea urchin sperm acrosome reaction.
2002,
Pubmed
,
Echinobase
Hirohashi,
Structural requirements for species-specific induction of the sperm acrosome reaction by sea urchin egg sulfated fucan.
2002,
Pubmed
,
Echinobase
Hirohashi,
High molecular mass egg fucose sulfate polymer is required for opening both Ca2+ channels involved in triggering the sea urchin sperm acrosome reaction.
2002,
Pubmed
,
Echinobase
Hirohashi,
Egg sialoglycans increase intracellular pH and potentiate the acrosome reaction of sea urchin sperm.
2002,
Pubmed
,
Echinobase
Hirohashi,
Store-operated calcium channels trigger exocytosis of the sea urchin sperm acrosomal vesicle.
2003,
Pubmed
,
Echinobase
Mourão,
Structural features of sulfated glycans from the tunic of Styela plicata (Chordata-Tunicata). A unique occurrence of L-galactose in sulfated polysaccharides.
1987,
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
Pereira,
A 2-sulfated, 3-linked alpha-L-galactan is an anticoagulant polysaccharide.
2002,
Pubmed
,
Echinobase
Pol-Fachin,
Depiction of the forces participating in the 2-O-sulfo-alpha-L-iduronic acid conformational preference in heparin sequences in aqueous solutions.
2008,
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,
Mild acid hydrolysis of sulfated fucans: a selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides.
2005,
Pubmed
,
Echinobase
Ravenscroft,
3-Deoxy-octulosonic-acid-containing hexasaccharide fragment of unusual core type isolated from Hafnia alvei 2 lipopolysaccharide.
1995,
Pubmed
Saito,
Enzymatic methods for the determination of small quantities of isomeric chondroitin sulfates.
1968,
Pubmed
Schüttelkopf,
PRODRG: a tool for high-throughput crystallography of protein-ligand complexes.
2004,
Pubmed
Su,
Cyclic GMP-specific phosphodiesterase-5 regulates motility of sea urchin spermatozoa.
2006,
Pubmed
,
Echinobase
Usov,
Structure of a sulfated xylogalactan from the calcareous red alga Corallina pilulifera P. et R. (Rhodophyta, Corallinaceae).
1997,
Pubmed
Vacquier,
Isolation of bindin: the protein responsible for adhesion of sperm to sea urchin eggs.
1977,
Pubmed
,
Echinobase
Van Der Spoel,
GROMACS: fast, flexible, and free.
2005,
Pubmed
Verli,
Molecular dynamics simulation of a decasaccharide fragment of heparin in aqueous solution.
2004,
Pubmed
Verli,
Insights into the induced fit mechanism in antithrombin-heparin interaction using molecular dynamics simulations.
2005,
Pubmed
Vieira,
Structure of a fucose-branched chondroitin sulfate from sea cucumber. Evidence for the presence of 3-O-sulfo-beta-D-glucuronosyl residues.
1991,
Pubmed
,
Echinobase
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
Woods,
Three-dimensional structures of oligosaccharides.
1995,
Pubmed
