Randomized Combinatorial Library of Heteroglycoclusters (hGC)

Duléry, Vincent; Renaudet, Olivier; Wilczewski, Marie; Heyden, Angéline Van der; Labbé, Pierre; Dumy, Pascal

doi:10.1021/cc800029v

Cited by 25 publications

(18 citation statements)

References 35 publications

(21 reference statements)

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“…Neoglycoproteins to study influence of fucose or bisect (André, et al, 2007b) (Glycans) 4 and (amino acids) 4 on cyclopentapeptide TOF Sugars = αMan, αGalNAc, βLac, and αFuc; amino acids = Lys, Asp, Tyr, Phe, and Ile (Duléry, et al, 2008) C-Glycosylmethyl pyridylalanines Hantzsch-type three-component synthesis TOF TOF (DHB) A-Dystroglycan mucin domain…”

Section: Glycopeptides/glycoproteinsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Glycopeptides/glycoproteinsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…In this paper we have described an expedient and controlled assembly protocol to prepare heteroglycoclusters similar to those obtained previously from randomized combinatorial libraries [26]. Following two orthogonal chemoselective reactions, cyclopeptides 4 and 7 were successively reacted with aminooxy glycosyls 1 – 3a and propargyl glycosides 1 – 3b.…”

Section: Resultsmentioning

confidence: 99%

“…Although recognition mechanisms are not fully understood, these studies suggest that heteroglycoclusters should interact with proteins through distinct binding sites, which may influence both affinity and selectivity [11–25]. In this context, we previously reported a combinatorial procedure to prepare libraries of heteroglycoclusters displaying sugars and/or amino acids at randomized positions on a topological cyclopeptide scaffold [26]. Deconvolution of the resulting libraries by affinity chromatography allowed the selection of heteroglycoclusters that were proved to be useful for exploring the surrounding regions of the binding pocket in a model lectin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

Thomas¹,

Fiore²,

Bossu³

et al. 2012

Beilstein J. Org. Chem.

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SummarySynthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohydrates. By using both oxime ligation and copper(I)-catalyzed alkyne–azide cycloaddition, two series of compounds bearing binary combinations of αMan, αFuc or βLac in an overall tetravalent presentation, and either 2:2 or 3:1 relative proportions, have been prepared.

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“…35 Scheme 7 General procedure of combined amidative oxidation-click strategy to obtain Man/Gal-glycooligonucleotides. building block had been incorporated on the DNA synthesizer (38). This cycle was repeated a second time with the next glycodendron to afford a (Man) 3 (Glc) 3 conjugate (39, Scheme 8).…”

Section: )mentioning

confidence: 99%

Multivalency in heterogeneous glycoenvironments: hetero-glycoclusters, -glycopolymers and -glycoassemblies

2013

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Despite efficiently imitating functional ligand presentations in terms of valency and density, most of the reported multivalent carbohydrate prototypes barely reflect the inherent heterogeneity of biological systems, therefore underestimating the potential contribution of synergistic or antagonistic effects to molecular recognition events. To address this question, the design of novel molecular and supramolecular entities displaying different saccharide motifs in a controlled manner is of critical importance. In this review we highlight the current efforts made to synthesize heteromultivalent glycosystems on different platforms (peptides, dendrimers, polymers, oligonucleotides, calixarenes, cyclodextrins, microarrays, vesicles) and to evaluate the influence of heterogeneity in carbohydrateprotein (lectin, antibody) recognition phenomena. Although the number of publications on this topic is limited as compared to the huge volume of reports on homomultivalent sugar displays, the current body of results has already unravelled the existence of new binding mechanisms that operate in heterogeneous environments whose exact biological significance remains to be unveiled.

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Randomized Combinatorial Library of Heteroglycoclusters (hGC)

Cited by 25 publications

References 35 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

Multivalency in heterogeneous glycoenvironments: hetero-glycoclusters, -glycopolymers and -glycoassemblies

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