Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• infected trimannose treated wild-type mice in both the latex bead 1 and bioerodible microparticle 2 studies suggests that the new trimannose-linked bioerodible microparticles 2 are a safe and viable tool for presenting glycodendrimers to mammalian immune systems. The new construct of the bioerodible

Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• mediated interactions. Dynamic light scattering and fluorescence microscopy were used to study the multivalent interaction of galectin-1 with the glycodendrimers in solution, and glycodendrimers were observed to organize galectin-1 into nanoparticles. In the presence of a large excess of galectin-1

• , glycodendrimers nucleated galectin-1 into nanoparticles that were remarkably homologous in size (400–500 nm). To understand augmentation of oncologic cellular aggregation by galectin-1, glycodendrimers were used in cell-based assays with human prostate carcinoma cells (DU145). The results revealed that

• glycodendrimers provided competitive binding sites for galectin-1, which diverted galectin-1 from its typical function in cellular aggregation of DU145 cells. Keywords: dendrimer; galectin-1; glycodendrimer; multivalent; nanoparticle; Introduction Galectin-1 is a multivalent protein that mediates biological

DNA display of glycoconjugates to emulate oligomeric interactions of glycans

• Alexandre Novoa and
• Nicolas Winssinger

Beilstein J. Org. Chem. 2015, 11, 707–719, doi:10.3762/bjoc.11.81

• the geometry of the oligomeric interactions provided an important precedent [10] and has stimulated intense research in glycomimetics, glycodendrimers, and glycopolymers [11][12]. Over the past decade, there has been a growing interest in using oligonucleotide hybridization [13][14][15] to scaffold

Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency

• Anna K. Ciuk and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 668–674, doi:10.3762/bjoc.11.75

• [6]. This work is based on the idea that changes of ligand orientation as well as changes of their conformational availability are regulating parameters in carbohydrate recognition, in particular on the cell surface. Indeed, we have formerly shown that the molecular dynamics of glycodendrimers

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• lectins in the form of glycoclusters [17], poly(glycomer)s [18][19][20][21], and glycodendrimers [22][23][24]. In regards to PA, C-fucosylpeptide dendrimers were shown to inhibit biofilm formation and to efficiently disperse established biofilms in both reference and hospital strains of PA [25][26][27

• ]. Recently, galactosylated peptide dendrimers have shown a strong affinity for lecA while inhibiting or dispersing biofilms [28][29]. This anti-biofilm effect mediated by glycodendrimers validates a new approach to the control PA propagation and infection. In this work and following those lines, we had in

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• ; galectin-3; glycodendrimers; multivalency; multivalent glycosylation; protein aggregation; Introduction The role of multivalency in biology is well established, and examples of this phenomenon abound [1]. The ability of multivalency to enhance weak interactions has been shown in a variety of

• binding of galectins, as demonstrated in galectin binding studies with neuroblastoma cells [25]. Here, we demonstrate that glycodendrimers bearing lactose can be used to form large, discrete aggregates of galectin-3. Since, as noted above, glycan clustering and galectin-3-mediated aggregations have been

• demonstrated to be important for biological interactions ranging from bacterial invasion to cancer cellular responses, the development of systems such as glycodendrimers that can aggregate galectin-3 into nanoparticles in a highly controlled fashion is an important area of research. The study of galectin-3

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• 9-mer 12, 17, and 21 were determined by pulsed-field-gradient-stimulated echo (PFG-STE) NMR experiments and were found to be 3.0, 2.5, and 3.4 nm, respectively. Keywords: carbohydrates; click chemistry; dendrimers; glycodendrimers; lectins; multivalent glycosystems; Introduction Multivalent

• ], glycodendrimers [7][8][9][10][11][12][13][14], and sugar rods [15][16] have retained most attention. An additional approach that has gained keen interest resides in the modifications of both the aglycon [17][18][19] and substituent residues [20][21][22] of the targeted sugar moieties through extensive studies of

• more insight into this direction, we designed herein three families of closely related mannopyranoside clusters (glycodendrimers) aimed at evaluating their relative binding abilities against the hometetrameric leguminous lectin ConA from Canavalia ensiformis by inhibition of haemagglutination and by

Postsynthetic functionalization of glycodendrons at the focal point

• Thisbe K. Lindhorst and
• Katharina Elsner

Beilstein J. Org. Chem. 2014, 10, 1482–1487, doi:10.3762/bjoc.10.152

• example the glycodendrimers, have become valuable tools during the last two decades [2]. Typical glycodendrimers consist of (hyper)branched dendritic core molecules which are decorated with specific sugars in their periphery [3][4][5]. In addition to dendrimers, also so-called dendrons have been

Design and synthesis of multivalent neoglycoconjugates by click conjugations

• Feiqing Ding,
• Li Ji,
• Ronny William,
• Hua Chai and
• Xue-Wei Liu

Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

• monovalent affinities of carbohydrate monosaccharides are comparatively low and weak. To enhance this multivalent effect, thereby increasing the binding efficiencies of carbohydrates with the coupling counterparts, there has been a constant development of new glycoconjugates such as glycodendrimers [57

A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

• El Sayed H. El Ashry,
• El Sayed H. El Tamany,
• Mohy El Din Abdel Fattah,
• Mohamed R. E. Aly,
• Ahmed T. A. Boraei and
• Axel Duerkop

Beilstein J. Org. Chem. 2013, 9, 135–146, doi:10.3762/bjoc.9.16

• ]. Glycosylamines are used also as enzyme inhibitors and vaccine precursors [18][19][20][21], and in glycopeptide synthesis [22][23] and in glycodendrimers and glycoclusters [24][25]. There are four structural isomers of glycosyl-thiosemicarbazides according to the location of the glycosyl residue on the

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• variety of useful conjugation reactions, including mono- as well as oligo- and polyvalent amines, and the carbohydrate decoration of functionalized surfaces. Fields of application concern the construction of oligovalent glycoconjugates, such as glycoclusters and glycodendrimers, the modification of

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• units. With the purpose of expanding the valency and increasing the glycoside density, glycodendrimers have also been synthesised and their properties in protein–carbohydrate interactions have been studied [24][25][26]. However, the innovative frontier of combining glycodendrimeric arrangements onto a