Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:<sup>1</sup>Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides

Khatuntseva, Elena A.; Ustuzhanina, Nadezhda E.; Zatonskii, G. V.; Shashkov, Alexander S.; Усов, А. И.; Nifant'ev, Nikolay E.

doi:10.1080/07328300008544140

Cited by 54 publications

(30 citation statements)

References 48 publications

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“…17 However, activity among fucoidans clearly depends on the shape and charge features of some fragments. 18 The group of Nifantiev has started a series of papers reporting the synthesis and conformational studies of fucoidan fragments. 18 They have presented the first PES analysis for such fragments and compare them with experimentally determined features.…”

Section: Introductionmentioning

confidence: 99%

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mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Stortz

2004

Carbohydrate Research

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Section: Introductionmentioning

confidence: 99%

“…18 The group of Nifantiev has started a series of papers reporting the synthesis and conformational studies of fucoidan fragments. 18 They have presented the first PES analysis for such fragments and compare them with experimentally determined features. 19,20 In connection with our work on bioactive fucoidans, 14 …”

Section: Introductionmentioning

confidence: 99%

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Stortz

2004

Carbohydrate Research

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“…17 The Nifantiev group has presented extensive work synthesizing di-, tri-, tetra-, hexa-, octa-, dodeca-and hexadecafucosides with various differences in branching-, sulfation-and fucosidic linkage patterns. [18][19][20][21][22][23][24][25] These fucoidan fragments were subjected to extensive conformational studies through NMR, [18][19][20][21][22][23]25 yet no biological activity studies have been published. We also noted that all the synthetic fucoidan fragments referred to were produced through saccharide formation, which is often time-consuming and results in poor yields with growing saccharide chain length.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Fucoidan-Mimetic Glycopolymers through Cyanoxyl-Mediated Free-Radical Polymerization

Tengdelius¹,

Lee²,

Grenegård

et al. 2014

Biomacromolecules

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The sulfated marine polysaccharide fucoidan has been reported to have health benefits ranging from antivirus and anticancer properties to modulation of high blood pressure. Hence, they could enhance the biological function of materials for biomedical applications. However, the incorporation of fucoidan into biomaterials has been difficult, possibly due to its complex structure and lack of suitable functional groups for covalent anchoring to biomaterials. We have developed an approach for a rapid synthesis of fucoidan-mimetic glycopolymer chains through cyanoxyl-mediated free-radical polymerization, a method suitable for chain-end functionalizing and subsequent linkage to biomaterials. The resulting sulfated and nonsulfated methacrylamido α-L-fucoside glycopolymers' fucoidan-mimetic properties were studied in HSV-1 infection and platelet activation assays. The sulfated glycopolymer showed similar properties to natural fucoidan in inducing platelet activation and inhibiting HSV-1 binding and entry to cells, thus indicating successful syntheses of fucoidan-mimetic glycopolymers.

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“…For the synthesis of the compounds OS1-OS5 the efficient method of the α-l-fucosylation has been developed [27,[30][31][32]. The stereoselectivity of the reaction is determined by the presence of acyl groups at O-3 and/or O-4 of a fucosyl donor, which stabilize the glycosyl cation in a manner favorable for the α-attack …”

Section: Synthesis Of the Oligosaccharides Related To Fucoidansmentioning

confidence: 99%

Fucoidans as a platform for new anticoagulant drugs discovery

Ustyuzhanina

Ушакова

Preobrazhenskaya

et al. 2014

Pure and Applied Chemistry

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Anionic fucose-containing polysaccharides (fucoidans of brown seaweeds, sulfated fucans and fucosylated chondroitin sulfates of invertebrates) are attracting a rapidly growing research interest due to different types of their biological activity discovered in recent years. In particular, algal fucoidans are characterized by large structural variations depending on the species used for their isolation and by the lack of structural regularity due to random distribution of both carbohydrate and non-carbohydrate substituents along the polymer chains. These features make it difficult to find distinct correlations between structural elements and biological properties of polysaccharides. Nevertheless, there is expectation that systematic structural and biochemical studies of fucoidans will form a basis for the development of new drugs. Herewith we summarize our recent results on the influence of fucoidan structure on blood coagulation.

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Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:¹Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides

Cited by 54 publications

References 48 publications

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Synthesis and Biological Evaluation of Fucoidan-Mimetic Glycopolymers through Cyanoxyl-Mediated Free-Radical Polymerization

Fucoidans as a platform for new anticoagulant drugs discovery

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Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:1Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides

Cited by 54 publications

References 48 publications

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Synthesis and Biological Evaluation of Fucoidan-Mimetic Glycopolymers through Cyanoxyl-Mediated Free-Radical Polymerization

Fucoidans as a platform for new anticoagulant drugs discovery

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Synthesis, NMR and Conformational Studies of Fucoidan Fragments 1:¹Desulfated 2,3- and 3,4-Branched Trisaccharide Fragments and Constituting Disaccharides