Design of Triazole‐Tethered Glycoclusters Exhibiting Three Different Spatial Arrangements and Comparative Study of their Affinities towards PA‐IL and RCA 120 by Using a DNA‐Based Glycoarray

Sugar‐coated chips: Glycoside clusters are valuable tools for carbohydrate–lectin recognition studies. However, the spatial arrangement of the sugar residues is a key issue in the design of high‐affinity glycoclusters. Here the affinities of linear and antenna‐ and calixarene‐based galactoside clusters towards two lectins derived from Pseudomonas aeruginosa and Ricinus communis were compared by means of glycoarrays.

[1]  J. Vasseur,et al.  DNA-directed immobilisation of glycomimetics for glycoarrays application: comparison with covalent immobilisation, and development of an on-chip IC50 measurement assay. , 2009, Biosensors & bioelectronics.

[2]  Morten Meldal,et al.  Cu-catalyzed azide-alkyne cycloaddition. , 2008, Chemical reviews.

[3]  A. Vecchi,et al.  Microwave-enhanced ionothermal CuAAC for the synthesis of glycoclusters on a calix[4]arene platform. , 2008, The Journal of organic chemistry.

[4]  J. Vasseur,et al.  Combinatorial and automated synthesis of phosphodiester galactosyl cluster on solid support by click chemistry assisted by microwaves. , 2008, The Journal of organic chemistry.

[5]  J. Kopitz,et al.  Calix[n]arene‐Based Glycoclusters: Bioactivity of Thiourea‐Linked Galactose/Lactose Moieties as Inhibitors of Binding of Medically Relevant Lectins to a Glycoprotein and Cell‐Surface Glycoconjugates and Selectivity among Human Adhesion/Growth‐Regulatory Galectins , 2008, Chembiochem : a European journal of chemical biology.

[6]  A. Marra,et al.  Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses. , 2008, Organic & biomolecular chemistry.

[7]  J. Cloarec,et al.  Low-cost, fast prototyping method of fabrication of the microreactor devices in soda-lime glass , 2008 .

[8]  J. Lietard,et al.  New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves. , 2008, The Journal of organic chemistry.

[9]  J. Hacker,et al.  Inhibition of P-fimbriated Escherichia coli adhesion by multivalent galabiose derivatives studied by a live-bacteria application of surface plasmon resonance. , 2007, The Journal of antimicrobial chemotherapy.

[10]  E. Goddard-Borger,et al.  An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. , 2007, Organic letters.

[11]  A. Imberty,et al.  Fucosylated pentaerythrityl phosphodiester oligomers (PePOs): automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL). , 2007, Bioconjugate chemistry.

[12]  J. Moses,et al.  The growing applications of click chemistry. , 2007, Chemical Society reviews.

[13]  A. Marra,et al.  Addressing the scope of the azide–nitrile cycloaddition in glycoconjugate chemistry. The assembly of C-glycoclusters on a calix[4]arene scaffold through tetrazole spacers , 2007 .

[14]  A. Dondoni Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction. , 2007, Chemistry, an Asian journal.

[15]  T. Brown,et al.  Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry. , 2007, Journal of the American Chemical Society.

[16]  Peng Wu,et al.  Catalytic Azide—Alkyne Cycloaddition: Reactivity and Applications , 2007 .

[17]  J. Vasseur,et al.  DNA-based carbohydrate biochips: a platform for surface glyco-engineering. , 2007, Angewandte Chemie.

[18]  R. Field,et al.  Recent applications of the Cu(I)-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry. , 2007, Organic & biomolecular chemistry.

[19]  J. Lutz 1,3‐Dipolare Cycloaddition von Aziden und Alkinen: eine universelle Ligationsmethode in den Polymer‐ und Materialwissenschaften , 2007 .

[20]  Jean-François Lutz,et al.  1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. , 2007, Angewandte Chemie.

[21]  A. Marra,et al.  C-glycoside clustering on calix[4]arene, adamantane, and benzene scaffolds through 1,2,3-triazole linkers. , 2006, The Journal of organic chemistry.

[22]  J. Vasseur,et al.  Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support. , 2006, The Journal of organic chemistry.

[23]  N. Pant,et al.  Regioselective ipso formylation of p-tert-butylcalix[4]arene , 2005 .

[24]  Eliane Souteyrand,et al.  Immobilization of single-stranded DNA fragments to solid surfaces and their repeatable specific hybridization: covalent binding or adsorption? , 2004 .

[25]  Injae Shin,et al.  Carbohydrate chips for studying high-throughput carbohydrate-protein interactions. , 2004, Journal of the American Chemical Society.

[26]  A. Imberty,et al.  Structures of the lectins from Pseudomonas aeruginosa: insight into the molecular basis for host glycan recognition. , 2004, Microbes and infection.

[27]  K. Matsuura,et al.  Self-organized glycoclusters along DNA: effect of the spatial arrangement of galactoside residues on cooperative lectin recognition. , 2004, Chemistry.

[28]  F. Nakajima,et al.  Glycotentacles: synthesis of cyclic glycopeptides, toward a tailored blocker of influenza virus hemagglutinin. , 2003, Angewandte Chemie.

[29]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[30]  Xubo Hu,et al.  Glycoside-Clustering Round Calixarenes toward the Development of Multivalent Carbohydrate Ligands. Synthesis and Conformational Analysis of Calix[4]arene O- and C-Glycoconjugates , 2002 .

[31]  R. Roy,et al.  Glycodendrimers: novel glycotope isosteres unmasking sugar coding. case study with T-antigen markers from breast cancer MUC1 glycoprotein. , 2002, Journal of biotechnology.

[32]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[33]  E. Toone,et al.  The cluster glycoside effect. , 2002, Chemical reviews.

[34]  Santoyo-González,et al.  Regioselective Monoalkylation of Calixarenes. Synthesis of Homodimer Calixarenes. , 2000, The Journal of organic chemistry.

[35]  W. Chung,et al.  Synthesis of Calix[4]arenes with Four Different "Lower Rim" Substituents. , 1999, The Journal of organic chemistry.

[36]  A. Vasella,et al.  Novel Type of Rigid C-Linked Glycosylacetylene−Phenylalanine Building Blocks for Combinatorial Synthesis of C-linked Glycopeptides , 1998 .

[37]  A. Marra,et al.  Synthesis of Calix[4]arenylvinylene and Calix[4]arenylphenylene Oligomers by Stille and Suzuki Cross-Coupling Reactions , 1998 .

[38]  N. Sharon,et al.  Lectins: Carbohydrate-Specific Proteins That Mediate Cellular Recognition. , 1998, Chemical reviews.

[39]  F. Sansone,et al.  Synthesis and Properties of O‐Glycosyl Calix[4]Arenes (Calixsugars) , 1997 .

[40]  V. Böhmer SPECIAL CALIXARENES BY DIRECTED SYNTHESES , 1997 .

[41]  Atsushi Ikeda,et al.  Novel Cavity Design Using Calix[n]arene Skeletons: Toward Molecular Recognition and Metal Binding. , 1997, Chemical reviews.

[42]  J. Rebek,et al.  Polycaps: reversibly formed polymeric capsules. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[43]  Lee-Gin Lin,et al.  p-triallylcalix[4]arene: The final member of the p-allylcalix[4]arenes , 1996 .

[44]  F. Sansone,et al.  Calixsugars:† Preparation of Upper Rim O-Ketopyranosyl Calix[4]arenes† , 1996 .

[45]  Yuan-chuan Lee,et al.  Carbohydrate-Protein Interactions: Basis of Glycobiology , 1995 .

[46]  T. V. van Berkel,et al.  Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor. , 1995, Journal of medicinal chemistry.

[47]  V. Böhmer Calixarenes, Macrocycles with (Almost) Unlimited Possibilities , 1995 .

[48]  V. Böhmer Calixarene – Makrocyclen mit (fast) unbegrenzten Möglichkeiten , 1995 .

[49]  R. Ungaro,et al.  Calix[4]arenes Blocked in a Rigid Cone Conformation by Selective Functionalization at the Lower Rim , 1995 .

[50]  A. Marra,et al.  Sugar Calixarenes: Preparation of Calix[4]arenes Substituted at the Lower and Upper Rims with O‐Glycosyl Groups , 1995 .

[51]  A. Dondoni,et al.  Zuckercalixarene: Synthese von Calix[4]arenen mit O‐Glycosylsubstituenten am oberen oder unteren Rand , 1994 .

[52]  J. Knowles,et al.  Ligand recognition by influenza virus. The binding of bivalent sialosides. , 1991, The Journal of biological chemistry.

[53]  D. Reinhoudt,et al.  Synthesis of Monoalkylated Calix(4)arenes via Direct Alkylation , 1991 .

[54]  S. Shinkai,et al.  Conformations and structures of tetra-O-alkyl-p-tert-butylcalix[4]arenes. How is the conformation of calix[4]arenes immobilized? , 1991 .

[55]  D. Reinhoudt,et al.  SELECTIVE FUNCTIONALIZATION OF CALIX(4)ARENES AT THE UPPER RIM , 1990 .

[56]  N. Firon,et al.  Aromatic alpha-glycosides of mannose are powerful inhibitors of the adherence of type 1 fimbriated Escherichia coli to yeast and intestinal epithelial cells , 1987, Infection and immunity.

[57]  C. Gutsche,et al.  Calixarenes. 17. Functionalized calixarenes: the Claisen rearrangement route , 1985 .

[58]  R. Townsend,et al.  Binding of synthetic oligosaccharides to the hepatic Gal/GalNAc lectin. Dependence on fine structural features. , 1983, The Journal of biological chemistry.

[59]  C. Bewley Protein-carbohydrate interactions in infectious diseases , 2006 .

[60]  H. Hiemstra,et al.  CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective , 2005 .

[61]  Yuan-chuan Lee,et al.  2 – Enhanced Biochemical Affinities of Multivalent Neoglycoconjugates , 1994 .

[62]  A. Casnati,et al.  A general synthesis of calix[4]arene monoalkyl ethers , 1991 .

[63]  S. Shinkai,et al.  Syntheses of all possible conformational isomers of O-alkyl-p-t-butylcalix[4]arenes , 1991 .

[64]  C. Gutsche,et al.  Calixarenes 9 : Conformational isomers of the ethers and esters of calix[4]arenes , 1983 .

[65]  M. Caruthers,et al.  Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis , 1981 .