Fucosylated Chondroitin Sulfates from the Body Wall of the Sea Cucumber Holothuria forskali

Panagos, Charalampos G.; Thomson, Derek; Moss, Claire; Hughes, Adam D.; Kelly, Maeve; Liu, Yan; Chai, Wengang; Venkatasamy, Radhakrishnan; Spina, Domenico; Page, Clive; Hogwood, John; Woods, Robert J.; Mulloy, Barbara; Bavington, Charles D.; Uhrı́n, Dušan

doi:10.1074/jbc.m114.572297

Cited by 95 publications

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References 86 publications

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“…Examples come from marine invertebrates and plants (Bachelet et al, 2009;Fitton, 2011;Kozlowski et al, 2011;Pomin, 2012;Gomes et al, 2015). An example is fucosylated chondroitin sulfate , for which there is strong evidence of a conformational similarity between the branched GAG and the Lewis-X glycan motif, that has high affinity for L-and P-selectins (Panagos et al, 2014).…”

Section: Heparin the Complement System And Innate Immunitymentioning

confidence: 99%

Pharmacology of Heparin and Related Drugs

et al. 2015

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Section: Heparin the Complement System And Innate Immunitymentioning

confidence: 99%

Pharmacology of Heparin and Related Drugs

et al. 2015

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“…Fucosylated chondroitin sulfate polysaccharide was isolated from the body wall of the sea cucumber, Holothuria forskalias, as described previously (Panagos et al 2014). The sample was depolymerised using a modified protocol (see Supplementary Information) for β-eliminative depolymerisation of carbohydrates in anhydrous solutions (Gao et al 2015).…”

Section: Methodsmentioning

confidence: 99%

“…In the native polysaccharide, the fucose ring is stacked above the neighbouring GlcNAc residue enabling formation of an unusual hydrogen bond from its H5 proton to the ring oxygen of GalNAc, as described previously (Panagos et al 2014;Aeschbacher et al 2017). β-elimination breaks the GalNAc(1→4)GlcA glycosidic bond, transforming fucose into a terminal unit of the newly formed oligosaccharides II and IV.…”

Section: (3 2)d Bird Rx Hsqcmentioning

confidence: 96%

“…The method is illustrated on an analysis of a mixture of oligosaccharides produced by β-eliminative depolymerisation (Gao et al 2015) of fucosylated chondroitin sulfate (fCS) isolated from the body wall of the sea cucumber Holothuria forskali (Panagos et al 2014). This mixture is referred to throughout the paper as "the fCS mixture".Fucosyalted chondroitin sulfates appear in a range of marine organisms (Chen et al 2011;Ustyuzhanina et al 2017Ustyuzhanina et al , 2016) and display a variety of biological roles and potential bio-medical applications (Panagos et al 2014;Nagase et al 1995;Mourao et al 1996;Borsig et al 2007).…”

mentioning

confidence: 99%

“…This mixture is referred to throughout the paper as "the fCS mixture".Fucosyalted chondroitin sulfates appear in a range of marine organisms (Chen et al 2011;Ustyuzhanina et al 2017Ustyuzhanina et al , 2016) and display a variety of biological roles and potential bio-medical applications (Panagos et al 2014;Nagase et al 1995;Mourao et al 1996;Borsig et al 2007). The studied fCS is composed of the following repeating trisaccharide unit, [→3)GalNAcβ4,6S(1→4) [FucαX(1→3)]GlcAβ(1→] n , where X stands for different sulfation patterns (S) of fucose.…”

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(3, 2)D 1H, 13C BIRDr,X-HSQC-TOCSY for NMR structure elucidation of mixtures: application to complex carbohydrates

2018

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Overlap of NMR signals is the major cause of difficulties associated with NMR structure elucidation of molecules contained in complex mixtures. A 2D homonuclear correlation spectroscopy in particular suffers from low dispersion of 1 H chemical shifts; larger dispersion of 13 C chemical shifts is often used to reduce this overlap, while still providing the proton-proton correlation information e.g. in the form of a 2D 1 H, 13 C HSQC-TOCSY experiment. For this methodology to work, 13 C chemical shift must be resolved. In case of 13 C chemical shifts overlap, 1 H chemical shifts can be used to achieve the desired resolution. The proposed (3, 2)D 1 H, 13 C BIRD r,X -HSQC-TOCSY experiment achieves this while preserving singlet character of cross peaks in the F 1 dimension. The required high-resolution in the 13 C dimension is thus retained, while the cross peak overlap occurring in a regular HSQC-TOCSY experiment is eliminated. The method is illustrated on the analysis of a complex carbohydrate mixture obtained by depolymerisation of a fucosylated chondroitin sulfate isolated from the body wall of the sea cucumber Holothuria forskali.

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A Modular Approach to a Library of Semi‐Synthetic Fucosylated Chondroitin Sulfate Polysaccharides with Different Sulfation and Fucosylation Patterns

Laezza

Iadonisi

Pirozzi

et al. 2016

Chemistry A European J

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Fucosylated chondroitin sulfate (fCS)-a glycosaminoglycan (GAG) found in sea cucumbers-has recently attracted much attention owing to its biological properties. In particular, a low molecular mass fCS polysaccharide has very recently been suggested as a strong candidate for the development of an antithrombotic drug that would be safer and more effective than heparin. To avoid the use of animal sourced drugs, here we present the chemical transformation of a microbial sourced unsulfated chondroitin polysaccharide into a small library of fucosylated (and sulfated) derivatives thereof. To this aim, a modular approach based on the different combination of only five reactions was employed, with an almost unprecedented polysaccharide branching by O-glycosylation as the key step. The library was differentiated for sulfation patterns and/or positions of the fucose branches, as confirmed by detailed 2D NMR spectroscopic analysis. These semi-synthetic polysaccharides will allow a wider and more accurate structure-activity relationship study with respect to those reported in literature to date.

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Fucosylated Chondroitin Sulfates from the Body Wall of the Sea Cucumber Holothuria forskali

Cited by 95 publications

References 86 publications

Pharmacology of Heparin and Related Drugs

Pharmacology of Heparin and Related Drugs

(3, 2)D 1H, 13C BIRDr,X-HSQC-TOCSY for NMR structure elucidation of mixtures: application to complex carbohydrates

A Modular Approach to a Library of Semi‐Synthetic Fucosylated Chondroitin Sulfate Polysaccharides with Different Sulfation and Fucosylation Patterns

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