Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

• Vojtěch Hamala,
• Lucie Červenková Šťastná,
• Martin Kurfiřt,
• Petra Cuřínová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

• enzymes [1][2][3][4][5][6][7]. The introduction of additional fluorine atoms into a monofluorinated carbohydrate is an attractive way of modulating the binding affinity and pharmacokinetic properties of fluorinated glycomimetics. Hydrophobic segments incorporating multiple C–F bonds could (1) reduce the

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

• Danny Lainé,
• Vincent Denavit,
• Olivier Lessard,
• Laurie Carrier,
• Charles-Émile Fecteau,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237

• ; polyfluorinated carbohydrates; polyfluoroalditol analogues; Introduction The biological significance of carbohydrates includes, but are not limited to, immune regulation, infection, and cancer metastasis. Research in the field of molecular biology allowed the discovery of glycomimetics to study various

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• ) hydrogen chloride salt after the acidic deprotection [37] (Scheme 5). During recent decades, the cyclic thioetherification strategy was widely applied in the synthesis of thietane-based square sugurs (thietanoses), and sulfur-containing glycomimetics of furanoses and pyranoses [38]. The first thietanose

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• inhibition of this adhesion process using glycomimetics as pathoblockers has developed as an area of active research in the last two decades [11][12]. Uropathogenic Escherichia coli (UPEC) is a major cause for chronic and recurrent urinary tract infections. These bacteria employ lectins in order to attach to

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

• Maroš Bella,
• Sergej Šesták,
• Ján Moncoľ,
• Miroslav Koóš and
• Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

• ], disaccharides or higher oligosaccharides [5][6] as well as multivalent [7][8] carbohydrate units have been developed. These glycomimetics and glycopeptides have also found applications as bioactive compounds [9][10]. One group of the scaffolds includes iminosugars [11][12] as analogues of the monosaccharides

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• glycosidases. Keywords: dendrimers; glycosidase inhibitors; iminosugars; multivalency; piperidine alkaloids; Introduction Iminosugars are well-known naturally occurring glycomimetics with a nitrogen atom replacing the endocyclic oxygen, mainly recognized as inhibitors of carbohydrate-processing enzymes

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

• single strand stretches that remain flexible. Such assemblies can also be generated in spatially addressable format using DNA microarrays. At the core of this technology is the ability to conjugate biologically relevant glycans or glycomimetics to nucleic acids. Herein, we present an update of the

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

• target for pharmacological intervention. Further investigations of the specific functions played by these lectins in PA biofilm formation will provide useful understanding, and ultimately a means of prevention of PA virulence. The creative design of glycomimetics that can interfere or can modulate the

Photoswitchable precision glycooligomers and their lectin binding

• Daniela Ponader,
• Sinaida Igde,
• Marko Wehle,
• Katharina Märker,
• Mark Santer,
• David Bléger and
• Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

• direct structure–property correlations and a deeper insight into the multivalent binding of glycomimetics. Through this knowledge we can predict the resulting affinity of a glycomacromolecule based on the number and spacing of sugar ligands attached to the scaffold [7][10][11]. Furthermore, it would be

• modelling for ligand binding. Ongoing studies further investigate ligand binding by additional techniques such as isothermal titration calorimetry and fluorescence spectroscopy. Overall, we have successfully developed photoswitchable glycomimetics that allow for a stimulus-induced change in binding affinity

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

• carbohydrate–protein interactions are at the forefront of a wide range of biological events which have triggered a plethora of versatile synthetic methods for the design of potent inhibitors and glycomimetics [1][2][3][4]. Among the diverse strategies leading to efficient ligands, glycopolymers [1][5][6][7

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

• etherification, thiol-ene reaction and in particular olefin cross metathesis. Keywords: amphiphilic glycomimetics; cross metathesis; glycodendrons; multivalent glycoconjugates; multivalent glycosystems; Introduction In addition to nucleic acids and proteins, molecular life is based on a third important class

• of compounds, the carbohydrates. Carbohydrates are involved in numerous biological recognition processes, where they are often displayed in the form of multivalent conjugates such as on the surface of cells [1]. To investigate multivalency in carbohydrate recognition, multivalent glycomimetics, for

Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed–disarmed strategy

• Abhijeet K. Kayastha and
• Srinivas Hotha

Beilstein J. Org. Chem. 2013, 9, 2147–2155, doi:10.3762/bjoc.9.252

• glycoconjugates [24], carbohydrate epitopes present on the cell surface of infectious bacteria [25], glycopolypeptides [26], glycopolyacrylates [27], and glycomimetics [28]. The remarkable reactivity and chemoselectivity have also attracted other groups to investigate gold catalysts for glycosidation [29][30][31

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• polyvalent glycomimetics with regularly spaced cores to be used for Man-specific C-lectin inhibition assays. With access to structural data of target lectins, the design of multivalent inhibitors can be performed on a customized level, where the selection of the proper spacer is based on the information

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• , which can be promising targets for the synthesis of glycomimetics. To some extent, knowledge of such proteins can of course be found in classical protein or enzyme databases, such as UniProt (http://www.uniprot.org) [50] or BRENDA (http://www.brenda-enzymes.info) [51]. However, these databases do not

• challenge for glycoinformatics, but it also offers many possibilities to synthesize carbohydrates or glycomimetics that target specific pathogen proteins. For example, oligosaccharide motifs that are found in surface carbohydrates of pathogens, but not in host organisms or in symbiotes, can serve as

• templates in vaccine development [67][68][69][70], and glycomimetics that block specific enzymes or lectins can be used for therapeutic purposes [71][72][73][74][75][76][77]. The Glycan Pathway Prediction (GPP) tool of the RINGS portal [78] can be used to predict glycans that can be obtained with a given

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

• Ian Cumpstey,
• Jens Frigell,
• Elias Pershagen,
• Tashfeen Akhtar,
• Elena Moreno-Clavijo,
• Inmaculada Robina,
• Dominic S. Alonzi and
• Terry D. Butters

Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128

• glycosidase inhibitory activity. Keywords: amination; glycomimetics; glycosidases; Mitsunobu; pseudodisaccharides; Introduction We have been interested in synthesising molecules consisting of two monosaccharides linked by formal condensation without using the anomeric position [1]. Such molecules, termed

Carbasugar analogues of galactofuranosides: α-O-linked derivatives

• Jens Frigell and
• Ian Cumpstey

Beilstein J. Org. Chem. 2010, 6, 1127–1131, doi:10.3762/bjoc.6.129

• exemplify the method. Keywords: carbasugars; etherification; galactofuranose; glycomimetics; pseudodisaccharides; regioselective; Introduction Galactofuranose is found in nature as a component of glycoconjugates in many microorganisms [1][2]. Galactofuranosides with the α configuration are rather less

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• ; glycomimetics; pseudooligosaccharides; spaced sugars; Review Among the major classes of biomolecules, carbohydrates are characterized by nearly unlimited structural diversity. Monosaccharide units can combine to produce oligosaccharides in a number of permutations that increases rapidly with the number of

•  years, some reviews on SAAs have summarised the different synthetic methods used to obtain such molecules [12][13][14] as well as their applications to access to a diversity of linear, branched and cyclic pseudooligosaccharides and glycomimetics often referred to as carbopeptoids [13][14][15][16][17

Synthesis in the glycosciences

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2010, 6, No. 16, doi:10.3762/bjoc.6.16

• syntheses”. It is therefore not surprising that the majority of contributions collected in this Thematic Series deal with methods, both chemical and enzymatic, for oligosaccharide synthesis. One approach to deal with the problem of glycoside synthesis is the preparation of so-called glycomimetics. This is a

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• enzymes. The synthesis of these new C8-glycomimetics is described from enantiomerically pure C2-symmetrical polyhydroxylated cyclooctenes. Their obtention notably involved a syn-dihydroxylation, and more extended functionalization through formation of a cis-cyclic sulfate followed by amination and

• particular case, due to the hindered conformation of such epoxides as demonstrated by X-ray cristallographic analysis. Conclusion The biological activity of the synthesized glycomimetics has been evaluated towards 24 commercially available glycosidases. The weak observed activities can probably be related to

• the spatial disposition of the hydroxy and amino groups which depart too much from that realized in glycomimetics such as valiolamine, voglibose and valienamine. Nevertheless, the synthetic strategy described here is efficient and general, and could be extended to increase the diversity of the