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Synthesis of Glycoconjugates having bioactivities
Typically syntheses of glycoconjugates adopt one of two strategies. The first strategy is the formation of the glycan-aglycone link early, to form, for example, glycosylated building blocks such as glycosides, glycopeptides or glycosylated dendritic wedges, that may then be assembled. While, of course, chemical methods can create glycosidic bonds in a number of ways, the use of biocatalysts can bring with it advantages of selectivity and efficiency; Křen’s chapter highlights this utility well. The second strategy is formation of the link later on in the synthesis once the scaffold for its presentation is in place. Given the instability that may be associated with the link and the requirements for protection that need to be considered in the use of glycosylated building blocks, it is clear why the latter has often seemed the most attractive option. Peri has deftly summarized a broad range of methods for this late stage approach as applied to many useful platform types. Nativi et al. have delineated an emerging area that could allow access to glycomimetics based on the use of glycals in cycloadditions.
R., Activity-Based Protein Profiling Reagents for Protein Arginine Deaminase 4 (PAD4): Synthesis and in vitro Evaluation of a Fluorescently Labeled Probe.
Synthesis of pyrrolidinoporphyrin glycoconjugates.
R.; Lober, S.; Hubner, H.; Gmeiner, P., Click chemistry on solid phase: parallel synthesis of -benzyltriazole carboxamides as super-potent G-protein coupled receptor ligands.
B., Synthesis of azide-alkyne fragments for click' chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols.
H., His6 tag-assisted chemical protein synthesis.
Through the use of modern molecular biology techniques, it is possible to transfer individual enzymes from their host organism and produce them in more amenable laboratory strain bacteria. This allows them to be more easily studied, engineered and integrated into new enzyme cascades, both in whole cell systems and as cell-free formulations. In the Flitsch group we are interested in the tailoring of various enzymes to perform specific, synthetically-useful reactions and incorporating these into bespoke pathways for the production of industrially- and biomedically-relevant compounds. Examples of target products of particular interest include high value chiral amines as pharmaceutical / fine chemical precursors and glycoconjugates as chemical biology probes for glycobiotechnology.
Glen Research is delighted to introduce a GalNAc modification strategy using a monomeric GalNAc support and the equivalent GalNAc phosphoramidite. Our experimental work has shown that these products are fully compatible with regular oligonucleotide synthesis and deprotection. Oligonucleotides containing GalNAc can be deprotected using standard procedures during which the acetyl protecting groups on the GalNAc group are removed. Glen Research offers these GalNAc C3 products under an agreement with AM Chemicals LLC.
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Synthesis of rapamycin glycoconjugates via a CuAAC …
The authors note that the detailed studies of the molecular mechanisms of DNA repair pathways were made possible by using site-specifically modified oligonucleotides and that the availability of phosphoramidites to synthesize oligonucleotides with DNA lesions has contributed to the field. They illustrate the article using primarily structural studies in the following examples:
Synthesis and Biological Applications of Glycoconjugates
Our main motivation to edit was to update the major advancements in this field through several chapters written by renowned experts who have largely contributed to the recent progresses. Illustrated with more than 200 colour figures and including literature citations mostly from the last decade, this book covers the recent chemical methods of glycoconjugates and clearly highlights their diverse biological properties. analyzes the structure of lectins from pathogenic bacteria and gives structure/function relationships that are crucial for the development of high affinity ligands. In carbohydrate binding by FimH is discussed and modern means for its investigation including photoaffinity labelling are described. Very recent crystallographic work is also documented that provides an explanation for shear-enhanced binding of type 1 fimbriated E. coli. summarizes the most convenient methodologies for the synthesis of glycocalixarenes and describes their impressive aggregation properties and many other biological applications. illustrates examples of bacterial and human lectins together with bacterial toxins having varied number of carbohydrate recognition domains that necessitated multivalent glycoconjugates. It focuses on glycofullerenes that have been used to describe novel synthetic strategies and possible fit with concomitant lectins. In the structures of the cholera and E. coli heat-labile toxins are described. The authors also summarize the main strategies that have led to the development of monovalent and multivalent inhibitors of these toxins and they discuss the importance of chelation and protein aggregation as mechanisms of multivalent inhibition. focuses on the design of high affinity ligands for galectins and provides a better knowledge of the implications of these proteins in biology. demonstrates that combinatorial chemistry led to the discovery of glycopeptide dendrimers as strong ligands for lectins or drug-delivery systems and shows how the amino acid composition of the dendrimer branches can influence their biological activity. focuses on the synthesis of a recent class of glycoclusters displayed on a cyclopeptide platform and highlights their promising biological properties, in particular as inhibitors or synthetic vaccines. shows that the cellular delivery and bioavailability of oligonucleotides can be improved by their conjugation with carbohydrates and also describes the construction of carbohydrate biochips or glycoclusters using these conjugates. focuses on glycoliposomes and covalently-functionalized glyconanoparticles which make use of the “glyco-code” to address specifically pathogens or pathological-related problems. focuses on the synthesis of glycoproteins, glycopeptides, glycosylated natural compounds, carbohydrate-functionalized surfaces and nanoparticles using chemoselective glycosylation. In the recent developments in glycosidase-catalyzed synthesis of unnatural semi-synthetic carbohydrate structures are presented. reports the synthesis of glycomimetics and glycopeptidomimetics using hetero-Diels Alder reactions between α,α'-dioxothiones and glycals. aims at describing the usual methods to characterize protein-carbohydrate interactions, namely inhibition of hemagglutination assay, enzyme-linked lectin assays, isothermal titration calorimetry, surface plasmon resonance and the more recent atomic force microscopy.
Enzymes in the Synthesis of Glycoconjugates - …
The interactions between carbohydrates and proteins are involved in major physiological and pathological events. With the recent emergence of glycomics, an increasing number of sophisticated glycosylated structures capable of mimicking the multivalent display of the cell surface glycocalix has been reported. Besides giving precious guidelines on the binding parameters that govern these complex biological processes, synthetic glycoconjugates often revealed considerable interests for diagnostic and therapeutic applications.
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