A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

Renaudet, Olivier; Dumy, Pascal

doi:10.2174/1875398100801010001

Cited by 8 publications

(3 citation statements)

References 40 publications

(49 reference statements)

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“…More impressive linker effects were observed with the wheat germ agglutinin (WGA) β-GlcNAc-terminated tetravalent glycoclusters and thioether linker. 137 The same group designed series of labeled glycoclusters based on sequential attachment of various aminooxy sugars through an oxime bond onto the upper domain of the scaffold, having preinstalled either a biotin or a fluorescein molecule on the lower face, both in solution 138 and in the solid phase, 139 without mentioning biological properties.…”

Section: Glycoclustersmentioning

confidence: 99%

Aminooxylated Carbohydrates: Synthesis and Applications

et al. 2017

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Among other classes of biomolecules, carbohydrates and glycoconjugates are widely involved in numerous biological functions. In addition to addressing the related synthetic challenges, glycochemists have invested intense efforts in providing access to structures that can be used to study, activate, or inhibit these biological processes. Over the past few decades, aminooxylated carbohydrates have been found to be key building blocks for achieving these goals. This review provides the first in-depth overview covering several aspects related to the syntheses and applications of aminooxylated carbohydrates. After a brief introduction to oxime bonds and their relative stabilities compared to related C═N functions, synthetic aspects of oxime ligation and methodologies for introducing the aminooxy functionality onto both glycofuranosyls and glycopyranosyls are described. The subsequent section focuses on biological applications involving aminooxylated carbohydrates as components for the construcion of diverse architectures. Mimetics of natural structures represent useful tools for better understanding the features that drive carbohydrate-receptor interaction, their biological output and they also represent interesting structures with improved stability and tunable properties. In the next section, multivalent structures such as glycoclusters and glycodendrimers obtained through oxime ligation are described in terms of synthetic design and their biological applications such as immunomodulators. The second-to-last section discusses miscellaneous applications of oxime-based glycoconjugates, such as enantioselective catalysis and glycosylated oligonucleotides, and conclusions and perspectives are provided in the last section.

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Section: Glycoclustersmentioning

confidence: 99%

Aminooxylated Carbohydrates: Synthesis and Applications

et al. 2017

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“…The numerous successes encountered in the SPS of various peptide-based conjugates, coupled to the ease of preparation and purification of complex derivatives, have motivated chemists to apply this methodology to synthesis of peptide glycoclusters. Hence, linear peptides containing a glycocluster head group (172,173), 184 multivalent cyclic neoglycopeptides including, for instance, three N-acetylglucosamine residues (174), 185 and multitopic biotinylated glycoclusters build on a topological cyclodecapeptide template (175-179) 186 represent remarkable illustrations of this powerful and straightforward methodology ( Fig. 21).…”

Section: Glycoclusters From Peptide Scaffoldsmentioning

confidence: 99%

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

307

208

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From the authors' opinion, this chapter constitutes a modest extension of the seminal and inspiring contribution of Stowell and Lee on neoglycoconjugates published in this series [C. P. Stowell and Y. C. Lee, Adv. Carbohydr. Chem. Biochem., 37 (1980) 225-281]. The outstanding progresses achieved since then in the field of the "glycoside cluster effect" has witnessed considerable creativity in the design and synthetic strategies toward a vast array of novel carbohydrate structures and reflects the dynamic activity in the field even since the recent chapter by the Nicotra group in this series [F. Nicotra, L. Cipolla, F. Peri, B. La Ferla, and C. Radaelli, Adv. Carbohydr. Chem. Biochem., 61 (2007) 353-398]. Beyond the more classical neoglycoproteins and glycopolymers (not covered in this work) a wide range of unprecedented and often artistically beautiful multivalent and monodisperse nanostructures, termed glycodendrimers for the first time in 1993, has been created. This chapter briefly surveys the concept of multivalency involved in carbohydrate-protein interactions. The topic is also discussed in regard to recent steps undertaken in glycobiology toward identification of lead candidates using microarrays and modern analytical tools. A systematic description of glycocluster and glycodendrimer synthesis follows, starting from the simplest architectures and ending in the most complex ones. Presentation of multivalent glycostructures of intermediate size and comprising, calix[n]arene, porphyrin, cyclodextrin, peptide, and carbohydrate scaffolds, has also been intercalated to better appreciate the growing synthetic complexity involved. A subsection describing novel all-carbon-based glycoconjugates such as fullerenes and carbon nanotubes is inserted, followed by a promising strategy involving dendrons self-assembling around metal chelates. The chapter then ends with those glycodendrimers that have been prepared using commercially available dendrimers possessing varied functionalities, or systematically synthesized using either divergent or convergent strategies.

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“…26 We thus applied this methodology to a series of carbohydrate recognition motifs i.e. bGal 1, 27 aMan 2, 28 bLac 3 28 and the cancer-related antigen aTF 4, 29 which were obtained in 5 to 16 steps then successively conjugated to aldehyde-containing scaffolds using oxime ligation (Fig. 2).…”

Section: Synthesis Of Dendri-raftsmentioning

confidence: 99%

Dendri-RAFTs: a second generation of cyclopeptide-based glycoclusters

et al. 2011

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Synthetic glycoclusters and their related biological applications have stimulated increasing interest over the last decade. As a prerequisite to discovering active and selective therapeuticals, the development of multivalent glycoconjugates with diverse topologies is faced with inherent synthetic and structural characterisation difficulties. Here we describe a new series of molecularly-defined glycoclusters that were synthesized in a controlled manner using a robust and versatile divergent protocol. Starting from a Regioselectively Addressable Functionalized Template (RAFT) carrier, either a polylysine dendritic framework or a second RAFT, then 16 copies of βGal, αMan, βLac or cancer-related Thomsen-Freidenreich (αTF) antigen were successively conjugated within the same molecule using oxime chemistry. We thus obtained a new generation of dendri-RAFTs glycoclusters with high glycosidic density and variable spatial organizations. These compounds displaying 16 endgroups were unambiguously characterized by NMR spectroscopy and mass spectrometry. Further biological assays between a model lectin from Canavalia ensiformis (ConA) and mannosylated glycoclusters revealed a higher inhibition potency than the tetravalent counterpart, in particular for the hexadecavalent polylysine skeleton. Together with the efficiency of the synthetic and characterisation processes, this preliminary biological study provided clear evidence of promising properties that make the second generation of cyclopeptide-based glycoclusters attractive for biomedical applications.

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A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

Cited by 8 publications

References 40 publications

Aminooxylated Carbohydrates: Synthesis and Applications

Aminooxylated Carbohydrates: Synthesis and Applications

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Dendri-RAFTs: a second generation of cyclopeptide-based glycoclusters

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