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Glycobiology Advance Access published online on August 23, 2005
Glycobiology, doi:10.1093/glycob/cwj030
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© The Author 2005. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oupjournals.org
Received June 14, 2005
Revised August 1, 2005
Accepted August 17, 2005

Article

Mild acid hydrolysis of sulfated fucans: a selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides

Vitor H. Pomin 1, Ana Paula Valente 2, Mariana S. Pereira 3, and Paulo A.S. Mourão 1*

1 Laboratório de Tecido Conjuntivo, Hospital Universitário Clementino Fraga Filho; Instituto de Bioquímica Médica, Rio de Janeiro, RJ, 21941-590, Brazil
2 Instituto de Bioquímica Médica; Centro Nacional de Ressonância Magnética Nuclear Jiri Jonas, Rio de Janeiro, RJ, 21941-590, Brazil
3 Laboratório de Tecido Conjuntivo, Hospital Universitário Clementino Fraga Filho; Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, Caixa Postal 68041, Rio de Janeiro, RJ, 21941-590, Brazil

* To whom correspondence should be addressed.
Paulo A.S. Mourão, E-mail: pmourao{at}hucff.ufrj.br


  Abstract

Sulfated fucans from marine invertebrates have simple, linear structures, composed of repeating units of oligosaccharides. Most of these polysaccharides contain 3-linked fucosyl units but each species of invertebrate has a specific pattern of sulfation. No specific enzyme able to cleave or to desulfate these polysaccharides has been described yet. Therefore, we employed an alternative approach, based on mild acid hydrolysis, in an attempt to obtain low-molecular-weight derivatives from sulfated fucans. Surprisingly, we observed that sulfated fucans from Lytechinus variegatus and Strongylocentrotus pallidus (but not the sulfated fucans from other species) yield by mild acid hydrolysis oligosaccharides with well-defined molecular size as shown by narrow bands in polyacrylamide gel electrophoresis. The sulfated oligosaccharides obtained by mild acid hydrolysis were purified by gel-filtration chromatography and their structures were identified by 1H-NMR spectroscopy, revealing an identical chemical composition for all oligosaccharides. When we followed the acid hydrolysis by 1H-NMR spectroscopy we found that a selective 2-desulfation occurs in the fucans from S. pallidus and from L. variegatus. The reaction has two stages. Initially, 2-sulfate esters at specific sites are removed. Then the desulfated units are cleaved, yielding oligosaccharides with well-defined molecular size. The apparent requirement for the selective 2-desulfation is the occurrence of an exclusively 2-sulfated fucosyl unit linked to or preceded by a 4-sulfated residue. Thus, a homofucan from Strongylocentrotus franciscanus resists desulfation by mild acid hydrolysis because it lacks the neighboring 4-sulfated unit. Overall, our results show a new approach for desulfating sulfated fucans at specific sites and obtaining tailored sulfated oligosaccharides.

Keywords: sulfated polysaccharides/depolymerization/specific desulfation/sea urchin/low-molecular-weight fucans.
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