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Carbohydr Polym
2023 Feb 01;301Pt A:120316. doi: 10.1016/j.carbpol.2022.120316.
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Selective 2-desulfation of tetrasaccharide-repeating sulfated fucans during oligosaccharide production by mild acid hydrolysis.
Kim SB
,
Farrag M
,
Mishra SK
,
Misra SK
,
Sharp JS
,
Doerksen RJ
,
Pomin VH
.
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Sulfated fucans (SFs) from echinoderms, such as sea cucumbers and sea urchins, present linear and regular sulfation patterns within defined oligosaccharide building blocks. The high molecular weights of these polymers pose a problem in advanced structure-activity relationship studies for which derived oligosaccharides are more appropriate tools for investigation. However, enzymes capable of specifically depolymerizing SFs, fucanases, are not very common. Scarce abundance and unknown catalytic activities are additional barriers to exploiting fucanases. Oligosaccharide production by controlled chemical reactions such as mild acid hydrolysis then becomes a convenient strategy. As a consequence, physicochemical studies are necessary to understand the structural modifications caused on SFs by this chemical hydrolysis. Hence, in this work, we subjected three tetrasaccharide-repeating SFs from sea cucumbers, Isostichopus badionotus (IbSF), Holothuria floridana (HfSF), and Lytechinus variegatus (LvSF) to mild acid hydrolysis for oligosaccharide production. Interestingly, selective 2-desulfation reaction was observed in all three SFs. Through our study, we indicate that selective 2-desulfation is a common and expected phenomenon in oligosaccharide production by mild acid hydrolysis of SFs, including those composed of tetrasaccharide-repeating units.
An,
Oligosaccharide mapping analysis by HILIC-ESI-HCD-MS/MS for structural elucidation of fucoidan from sea cucumber Holothuria floridana.
2022, Pubmed,
Echinobase
An,
Oligosaccharide mapping analysis by HILIC-ESI-HCD-MS/MS for structural elucidation of fucoidan from sea cucumber Holothuria floridana.
2022,
Pubmed
,
Echinobase
Berteau,
Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide.
2003,
Pubmed
Bezerra,
Conformational properties of l-fucose and the tetrasaccharide building block of the sulfated l-fucan from Lytechinus variegatus.
2020,
Pubmed
,
Echinobase
Biermann,
Carbohydrate-based species recognition in sea urchin fertilization: another avenue for speciation?
2004,
Pubmed
,
Echinobase
Chen,
Sequence determination and anticoagulant and antithrombotic activities of a novel sulfated fucan isolated from the sea cucumber Isostichopus badionotus.
2012,
Pubmed
,
Echinobase
Chen,
Utilizing heterologously overexpressed endo-1,3-fucanase to investigate the structure of sulfated fucan from sea cucumber (Holothuria hilla).
2021,
Pubmed
,
Echinobase
Colin,
Cloning and biochemical characterization of the fucanase FcnA: definition of a novel glycoside hydrolase family specific for sulfated fucans.
2006,
Pubmed
Dwivedi,
Structural and kinetic analyses of holothurian sulfated glycans suggest potential treatment for SARS-CoV-2 infection.
2021,
Pubmed
,
Echinobase
Farndale,
A direct spectrophotometric microassay for sulfated glycosaminoglycans in cartilage cultures.
1982,
Pubmed
Kirschner,
GLYCAM06: a generalizable biomolecular force field. Carbohydrates.
2008,
Pubmed
Li,
Fucoidan: structure and bioactivity.
2008,
Pubmed
Li,
Mild acid hydrolysis on Fucan sulfate from Stichopus herrmanni: Structures, depolymerization mechanism and anticoagulant activity.
2022,
Pubmed
,
Echinobase
Luthuli,
Therapeutic Effects of Fucoidan: A Review on Recent Studies.
2019,
Pubmed
Ning,
A Fucan Sulfate with Pentasaccharide Repeating Units from the Sea Cucumber Holothuriafloridana and Its Anticoagulant Activity.
2022,
Pubmed
,
Echinobase
Oliveira,
Structural and functional analyses of biosimilar enoxaparins available in Brazil.
2015,
Pubmed
Panagos,
Fucosylated chondroitin sulfates from the body wall of the sea cucumber Holothuria forskali: conformation, selectin binding, and biological activity.
2014,
Pubmed
,
Echinobase
Pereira,
Structure and anticoagulant activity of sulfated fucans. Comparison between the regular, repetitive, and linear fucans from echinoderms with the more heterogeneous and branched polymers from brown algae.
1999,
Pubmed
,
Echinobase
Pereira,
Is there a correlation between structure and anticoagulant action of sulfated galactans and sulfated fucans?
2002,
Pubmed
Pomin,
Exploiting enzyme specificities in digestions of chondroitin sulfates A and C: production of well-defined hexasaccharides.
2012,
Pubmed
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,
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,
Structure, biology, evolution, and medical importance of sulfated fucans and galactans.
2008,
Pubmed
,
Echinobase
Queiroz,
Impact of sulfation pattern on the conformation and dynamics of sulfated fucan oligosaccharides as revealed by NMR and MD.
2015,
Pubmed
,
Echinobase
Roe,
PTRAJ and CPPTRAJ: Software for Processing and Analysis of Molecular Dynamics Trajectory Data.
2013,
Pubmed
Shi,
Comparison of hydrothermal depolymerization and oligosaccharide profile of fucoidan and fucosylated chondroitin sulfate from Holothuria floridana.
2019,
Pubmed
,
Echinobase
Teixeira,
Sulfated fucans and a sulfated galactan from sea urchins as potent inhibitors of selectin-dependent hematogenous metastasis.
2018,
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
WARREN,
The thiobarbituric acid assay of sialic acids.
1959,
Pubmed
Zsiska,
Influence of sulfate and carboxylate groups on the conformation of chondroitin sulfate related disaccharides.
1993,
Pubmed
