Progress and challenges in the synthesis of sequence controlled polysaccharides

Fittolani, Giulio; Tyrikos‐Ergas, Theodore; Vargová, Denisa; Chaube, Manishkumar A.; Delbianco, Martina

doi:10.3762/bjoc.17.129

Cited by 19 publications

(12 citation statements)

References 454 publications

(596 reference statements)

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“…Last, but not least, we feel this work represents a significant step forward in the molecular complexity achievable through a glycosylation reaction. Indeed, its employment is very well established in carbohydrate chemistry, − while its use for polysaccharide structural modification has been reported very seldom, in spite of its great potential for the obtainment of new polysaccharide-based biomaterials.…”

Section: Discussionmentioning

confidence: 99%

Semisynthetic Isomers of Fucosylated Chondroitin Sulfate Polysaccharides with Fucosyl Branches at a Non-Natural Site

et al. 2021

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The several interesting activities detected for fucosylated chondroitin sulfate (fCS) have fueled in the last years several efforts toward the obtainment of fCS oligosaccharides and low molecular weight (LMW) polysaccharides with a well-defined structure, in order to avoid the problems associated with the potential employment of native, sea cucumber sourced fCSs as a drug. Total synthesis and controlled depolymerization of the natural fCS polysaccharides are the main approaches to this aim; nonetheless, they present some limitations. These could be circumvented by semisynthesis, a strategy relying upon the regioselective fucosylation and sulfation of a microbial sourced polysaccharide sharing the same chondroitin backbone of fCS but devoid of any fucose (Fuc) and sulfate decoration on it. This approach is highly versatile, as it could open access also to fCS isomers carrying Fuc and sulfate groups at non-natural sites. Here we prepare for the first time some structurally homogeneous fCS isomers through a multistep procedure with a glycosylation reaction between a LMW polysaccharide acceptor and three different Fuc donors as key step. The obtained products were subjected to a detailed structural characterization by 2D-NMR. The conformational behavior was also investigated by NMR and molecular dynamics simulation methods and compared with data reported for natural fCS.

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Section: Discussionmentioning

confidence: 99%

Semisynthetic Isomers of Fucosylated Chondroitin Sulfate Polysaccharides with Fucosyl Branches at a Non-Natural Site

et al. 2021

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“…Compared to sulfated GAG, HA is a structurally uniform natural macromolecule and due to established biotechnological production processes it is readily available in higher quantities (Badri et al, 2018). Despite the progress achieved in the total synthesis of complex oligomeric carbohydrates (DeAngelis et al, 2013;Mende et al, 2016;Fittolani et al, 2021), HA represents an ideal starting material for the chemical conversion into other hardly accessible, mainly high-sulfated GAG or carbohydrate-analogous polymeric molecules mimicking their function, e.g., in the interactions with proteins like mediator molecules (e.g. cytokines).…”

Section: Introductionmentioning

confidence: 99%

Chemical Modification of Hyaluronan and Their Biomedical Applications

2022

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Hyaluronan, the extracellular matrix glycosaminoglycan, is an important structural component of many tissues playing a critical role in a variety of biological contexts. This makes hyaluronan, which can be biotechnologically produced in large scale, an attractive starting polymer for chemical modifications. This review provides a broad overview of different synthesis strategies used for modulating the biological as well as material properties of this polysaccharide. We discuss current advances and challenges of derivatization reactions targeting the primary and secondary hydroxyl groups or carboxylic acid groups and the N-acetyl groups after deamidation. In addition, we give examples for approaches using hyaluronan as biomedical polymer matrix and consequences of chemical modifications on the interaction of hyaluronan with cells via receptor-mediated signaling. Collectively, hyaluronan derivatives play a significant role in biomedical research and applications indicating the great promise for future innovative therapies.

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“…Upon sulfation, the removal of the residual PGs can be troublesome and further synthetic manipulations must avoid migration and/or cleavage of the labile sulfate moieties. 6 …”

Section: Introductionmentioning

confidence: 99%