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Eur J Mass Spectrom (Chichester)
2018 Feb 01;241:157-167. doi: 10.1177/1469066717731900.
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Structural elucidation of fucosylated chondroitin sulfates from sea cucumber using FTICR-MS/MS.
Agyekum I
,
Pepi L
,
Yu Y
,
Li J
,
Yan L
,
Linhardt RJ
,
Chen S
,
Amster IJ
.
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Fucosylated chondroitin sulfates are complex polysaccharides extracted from sea cucumber. They have been extensively studied for their anticoagulant properties and have been implicated in other biological activities. While nuclear magnetic resonance spectroscopy has been used to extensively characterize fucosylated chondroitin sulfate oligomers, we herein report the first detailed mass characterization of fucosylated chondroitin sulfate using high-resolution Fourier transform ion cyclotron resonance mass spectrometry. The two species of fucosylated chondroitin sulfates considered for this work include Pearsonothuria graeffei (FCS-Pg) and Isostichopus badionotus (FCS-Ib). Fucosylated chondroitin sulfate oligosaccharides were prepared by N-deacetylation-deaminative cleavage of the two fucosylated chondroitin sulfates and purified by repeated gel filtration. Accurate mass measurements obtained from electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry measurements confirmed the oligomeric nature of these two fucosylated chondroitin sulfate oligosaccharides with each trisaccharide repeating unit averaging four sulfates per trisaccharide. Collision-induced dissociation of efficiently deprotonated molecular ions through Na/H+ exchange proved useful in providing structurally relevant glycosidic and cross-ring product ions, capable of assigning the sulfate modifications on the fucosylated chondroitin sulfate oligomers. Careful examination of the tandem mass spectrometry of both species deferring in the positions of sulfate groups on the fucose residue (FCS-Pg-3,4- OS) and (FCS-Ib-2,4- OS) revealed cross-ring products 0,2Aαf and 2,4X2αf which were diagnostic for (FCS-Pg-3,4- OS) and 0,2X2αf diagnostic for (FCS-Ib-2,4- OS). Mass spectrometry and tandem mass spectrometry data acquired for both species varying in oligomer length (dp3-dp15) are presented.
Agyekum,
Single Stage Tandem Mass Spectrometry Assignment of the C-5 Uronic Acid Stereochemistry in Heparan Sulfate Tetrasaccharides using Electron Detachment Dissociation.
2017, Pubmed
Agyekum,
Single Stage Tandem Mass Spectrometry Assignment of the C-5 Uronic Acid Stereochemistry in Heparan Sulfate Tetrasaccharides using Electron Detachment Dissociation.
2017,
Pubmed
Agyekum,
Assignment Of Hexuronic Acid Stereochemistry In Synthetic Heparan Sulfate Tetrasaccharides With 2-O-Sulfo Uronic Acids Using Electron Detachment Dissociation.
2015,
Pubmed
Anastyuk,
Structural analysis of a highly sulfated fucan from the brown alga Laminaria cichorioides by tandem MALDI and ESI mass spectrometry.
2010,
Pubmed
Bienkowski,
Structural characterization of the oligosaccharides formed by depolymerization of heparin with nitrous acid.
1985,
Pubmed
Borsig,
Selectin blocking activity of a fucosylated chondroitin sulfate glycosaminoglycan from sea cucumber. Effect on tumor metastasis and neutrophil recruitment.
2007,
Pubmed
,
Echinobase
Ceroni,
GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans.
2008,
Pubmed
Chen,
Sulfation pattern of the fucose branch is important for the anticoagulant and antithrombotic activities of fucosylated chondroitin sulfates.
2013,
Pubmed
,
Echinobase
Damerell,
Annotation of glycomics MS and MS/MS spectra using the GlycoWorkbench software tool.
2015,
Pubmed
Daniel,
Electrospray ionization mass spectrometry of oligosaccharides derived from fucoidan of Ascophyllum nodosum.
2007,
Pubmed
Fonseca,
Fucosylated chondroitin sulfate as a new oral antithrombotic agent.
2006,
Pubmed
,
Echinobase
Fonseca,
Improved anticoagulant effect of fucosylated chondroitin sulfate orally administered as gastro-resistant tablets.
2017,
Pubmed
,
Echinobase
Fukuda,
Studies on the hydrazinolysis of glycoproteins. Core structures of oligosaccharides obtained from Porcine thyroglobulin and pineapple stem bromelain.
1976,
Pubmed
Glauser,
Serpin-independent anticoagulant activity of a fucosylated chondroitin sulfate.
2008,
Pubmed
,
Echinobase
Harvey,
Fragmentation of negative ions from carbohydrates: part 1. Use of nitrate and other anionic adducts for the production of negative ion electrospray spectra from N-linked carbohydrates.
2005,
Pubmed
Hu,
Identification of a highly sulfated fucoidan from sea cucumber Pearsonothuria graeffei with well-repeated tetrasaccharides units.
2015,
Pubmed
,
Echinobase
Huang,
An approach for separation and complete structural sequencing of heparin/heparan sulfate-like oligosaccharides.
2013,
Pubmed
Huang,
De novo sequencing of heparan sulfate oligosaccharides by electron-activated dissociation.
2013,
Pubmed
Huang,
LC-MS(n) analysis of isomeric chondroitin sulfate oligosaccharides using a chemical derivatization strategy.
2011,
Pubmed
Kailemia,
Structurally informative tandem mass spectrometry of highly sulfated natural and chemoenzymatically synthesized heparin and heparan sulfate glycosaminoglycans.
2013,
Pubmed
Kailemia,
Oligosaccharide analysis by mass spectrometry: a review of recent developments.
2014,
Pubmed
Kailemia,
Complete mass spectral characterization of a synthetic ultralow-molecular-weight heparin using collision-induced dissociation.
2012,
Pubmed
Kailemia,
Differentiating chondroitin sulfate glycosaminoglycans using collision-induced dissociation; uronic acid cross-ring diagnostic fragments in a single stage of tandem mass spectrometry.
2015,
Pubmed
Kariya,
Isolation and partial characterization of fucan sulfates from the body wall of sea cucumber Stichopus japonicus and their ability to inhibit osteoclastogenesis.
2004,
Pubmed
,
Echinobase
Kariya,
Occurrence of chondroitin sulfate E in glycosaminoglycan isolated from the body wall of sea cucumber Stichopus japonicus.
1990,
Pubmed
,
Echinobase
Leach,
Hexuronic acid stereochemistry determination in chondroitin sulfate glycosaminoglycan oligosaccharides by electron detachment dissociation.
2012,
Pubmed
Li,
Macromolecular properties and hypolipidemic effects of four sulfated polysaccharides from sea cucumbers.
2017,
Pubmed
,
Echinobase
Luo,
Comparison of physicochemical characteristics and anticoagulant activities of polysaccharides from three sea cucumbers.
2013,
Pubmed
,
Echinobase
Mourão,
Structure and anticoagulant activity of a fucosylated chondroitin sulfate from echinoderm. Sulfated fucose branches on the polysaccharide account for its high anticoagulant action.
1996,
Pubmed
,
Echinobase
Mourão,
Perspective on the use of sulfated polysaccharides from marine organisms as a source of new antithrombotic drugs.
2015,
Pubmed
Mourão,
Inactivation of thrombin by a fucosylated chondroitin sulfate from echinoderm.
2001,
Pubmed
,
Echinobase
Mourão,
Searching for alternatives to heparin: sulfated fucans from marine invertebrates.
1999,
Pubmed
Mulloy,
Structure/function studies of anticoagulant sulphated polysaccharides using NMR.
2000,
Pubmed
,
Echinobase
Myron,
Fucosylated chondroitin sulfate diversity in sea cucumbers: a review.
2014,
Pubmed
,
Echinobase
Nagase,
Depolymerized holothurian glycosaminoglycan with novel anticoagulant actions: antithrombin III- and heparin cofactor II-independent inhibition of factor X activation by factor IXa-factor VIIIa complex and heparin cofactor II-dependent inhibition of thrombin.
1995,
Pubmed
,
Echinobase
Pacheco,
Different antithrombotic mechanisms among glycosaminoglycans revealed with a new fucosylated chondroitin sulfate from an echinoderm.
2000,
Pubmed
,
Echinobase
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
Pomin,
Marine medicinal glycomics.
2014,
Pubmed
Rice,
Fractionation of heparin-derived oligosaccharides by gradient polyacrylamide-gel electrophoresis.
1987,
Pubmed
Stephens,
Fragmentation characteristics of neutral N-linked glycans using a MALDI-TOF/TOF tandem mass spectrometer.
2004,
Pubmed
Tao,
New insights into the action of bacterial chondroitinase AC I and hyaluronidase on hyaluronic acid.
2017,
Pubmed
Tissot,
Differentiation of the fucoidan sulfated L-fucose isomers constituents by CE-ESIMS and molecular modeling.
2006,
Pubmed
Ustyuzhanina,
The structure of a fucosylated chondroitin sulfate from the sea cucumber Cucumaria frondosa.
2017,
Pubmed
,
Echinobase
Ustyuzhanina,
Two fucosylated chondroitin sulfates from the sea cucumber Eupentacta fraudatrix.
2017,
Pubmed
,
Echinobase
Ustyuzhanina,
Variations of pH as an additional tool in the analysis of crowded NMR spectra of fucosylated chondroitin sulfates.
2016,
Pubmed
,
Echinobase
Ustyuzhanina,
Structure and biological activity of a fucosylated chondroitin sulfate from the sea cucumber Cucumaria japonica.
2016,
Pubmed
,
Echinobase
Vieira,
Occurrence of a unique fucose-branched chondroitin sulfate in the body wall of a sea cucumber.
1988,
Pubmed
,
Echinobase
Wolff,
Electron detachment dissociation of dermatan sulfate oligosaccharides.
2008,
Pubmed
Wolff,
Influence of charge state and sodium cationization on the electron detachment dissociation and infrared multiphoton dissociation of glycosaminoglycan oligosaccharides.
2008,
Pubmed
Wu,
Structure and effect of sulfated fucose branches on anticoagulant activity of the fucosylated chondroitin sulfate from sea cucumber Thelenata ananas.
2012,
Pubmed
,
Echinobase
Zaia,
Mass spectrometry and glycomics.
2010,
Pubmed
Zaia,
Tandem mass spectrometry of sulfated heparin-like glycosaminoglycan oligosaccharides.
2003,
Pubmed
Zaia,
Tandem mass spectrometric strategies for determination of sulfation positions and uronic acid epimerization in chondroitin sulfate oligosaccharides.
2003,
Pubmed
Zaia,
Glycosaminoglycan glycomics using mass spectrometry.
2013,
Pubmed
Zaia,
Mass spectrometry of oligosaccharides.
2004,
Pubmed
Zhao,
Collisionally activated dissociation and electron capture dissociation provide complementary structural information for branched permethylated oligosaccharides.
2008,
Pubmed
