From Chondroitin Polymer to Size‐Defined Hyaluronan Oligosaccharides

Lopez, Angelika Ferrer; Jacquinet, Jean‐Claude; Lopin‐Bon, Chrystel

doi:10.1002/ejoc.201300893

Cited by 8 publications

(1 citation statement)

References 32 publications

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“…With compound 51 in hand, unprotected hyaluronan di-, tri-, tetra-, and pentamers are easily accessible. The synthesis of the tetramer is depicted in Scheme . , …”

Section: Chemical Syntheses Of Glycosaminoglycans From Monosaccharidesmentioning

confidence: 99%

Chemical Synthesis of Glycosaminoglycans

et al. 2016

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Glycosaminoglycans (GAGs) as one major part of the glycocalyx are involved in many essential biological cell processes, as well as in many courses of diseases. Because of the potential therapeutic application of GAG polymers, fragments, and also derivatives toward different diseases (e.g., heparin derivatives against Alzheimer's disease), there is a continual growing demand for new chemical syntheses, which suffice the high claim to stereoselectivity and chemoselectivity. This Review summarizes the progress of chemical syntheses of GAGs over the last 10 years. For each class of the glycosaminoglycans-hyaluronan (HA), heparan sulfate/heparin (HS/HP), chondroitin/dermatan sulfate (CS/DS), and keratan sulfate (KS)-mainly novel glycosylation strategies, elongation sequences, and protecting group patterns are discussed, but also (semi)automated syntheses, enzymatic approaches, and functionalizations of synthesized or isolated GAGs are considered.

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“…With compound 51 in hand, unprotected hyaluronan di-, tri-, tetra-, and pentamers are easily accessible. The synthesis of the tetramer is depicted in Scheme . , …”

Section: Chemical Syntheses Of Glycosaminoglycans From Monosaccharidesmentioning

confidence: 99%

Chemical Synthesis of Glycosaminoglycans

et al. 2016

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Efficient Iterative Synthesis of O‐Acetylated Tri‐ to Pentadecasaccharides Related to the Lipopolysaccharide of Shigella flexneri Type 3 a through Di‐ and Trisaccharide Glycosyl Donors

White

Mulard

2017

Chemistry An Asian Journal

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Protection against bacterial infections, including shigellosis, can be achieved by antibodies against the bacterial surface polysaccharide. In line with our efforts to develop vaccine candidates for shigellosis, we report herein the synthesis of penta-, deca-, and pentadecasaccharides as well as tri-, octa-, and tridecasaccharides as the endchain and intrachain fragments, respectively, of the surface polysaccharide of Shigella flexneri 3 a, a prevalent serotype. The syntheses relied on the efficiency of the trichloroacetimidate glycosylation chemistry, whereby iteration with di- and trisaccharide building blocks provided fragments made of up to three mono-O-acetylated polysaccharide repeating units. Pd(OH) -mediated hydrogenation/hydrogenolysis enabled the concomitant removal or conversion of up to 31 protecting groups of 4 different origins to provide the targets as propyl glycosides. Oligosaccharides comprising the octasaccharide segment were shown to display high conformational similarities in solution.

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Chemical Synthesis of Modified Hyaluronic Acid Disaccharides

Mende

Nieger

Bräse

2017

Chemistry A European J

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Hereinw er eport ac hemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamineh ydrochloride. The variousp rotected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the b-d-glucuronic acid moiety with av iew to structure-related biological activityt ests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1 HNMR studies of the new derivatives demonstrated the effect of the variousf unctional groups on the intramolecularelectronic environment.

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From Chondroitin Polymer to Size‐Defined Hyaluronan Oligosaccharides

Cited by 8 publications

References 32 publications

Chemical Synthesis of Glycosaminoglycans

Chemical Synthesis of Glycosaminoglycans

Efficient Iterative Synthesis of O‐Acetylated Tri‐ to Pentadecasaccharides Related to the Lipopolysaccharide of Shigella flexneri Type 3 a through Di‐ and Trisaccharide Glycosyl Donors

Chemical Synthesis of Modified Hyaluronic Acid Disaccharides

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