One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• carbohydrate mimetics, but the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds. Keywords: alkynes; azides; copper catalysis; nucleophilic substitution; 1,2-oxazines; Introduction The concept of click reactions [1][2], in particular, the

• these results [37][38]. For several years, our group was interested in preparing multivalent carbohydrate mimetics [39][40][41][42][43] on the basis of efficient coupling reactions of aminopyran and aminooxepane derivatives with suitable linker elements. Hence, the aminopyran derivatives A could be

• good yields and furnished another set of multivalent carbohydrate mimetics [48][49][50]. In the current report, we want to disclose our experience with an “inverted” approach to multivalent systems [51]: bicyclic 1,2-oxazine derivatives of type G [52][53], which can be regarded as internally protected

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

• . Keywords: amino sugars; deoxyfluorination; fluorinated carbohydrates; hexosamine hemiacetals; thioglycosides; Introduction Fluorinated carbohydrates are versatile carbohydrate mimetics used to probe or manipulate the recognition of carbohydrates by carbohydrate-binding proteins or carbohydrate-processing

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

• Michal Medvecký,
• Igor Linder,
• Luise Schefzig,
• Hans-Ulrich Reissig and
• Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

• -alkoxy-γ-amino-aldehydes and ketones [14]. In this context, a series of publications of our group reported on syntheses of carbohydrate mimetics [15][16][17][18][19][20] that are based on aminopyrans, aminooxepanes or other aminopolyols and that were examined for example as ligands of L- and P-selectin

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

• Maroš Bella,
• Miroslav Koóš and
• Chun-Hung Lin

Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170

• simulate the shape and functionality of the natural substrates in the ground and/or the transition state (TS) of the enzymatic reaction [14]. In the case of GTs inhibitors, the carbohydrate mimetics that imitate the TS of the enzymatic reactions should exhibit a higher inhibition activity than the natural

• carbohydrate substrates [9][16]. Investigations of the catalytic mechanism of inverting glycosyltransferases [18] and N-acetylglucosaminyltransferase I [19] by employing ab initio calculations resulted in the design of inhibitors based on carbohydrate mimetics that simulate the transition state of the

Multivalency as a chemical organization and action principle

• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 848–849, doi:10.3762/bjoc.11.94

• [8][9][10][11][12] and studies the scope of multivalent lectin-glycointeractions in galectins [13], with iminosugars [14] and carbohydrate mimetics [15]. This Thematic Series in the Beilstein Journal of Organic Chemistry also investigates the enhanced multivalent binding of protein scaffolds [16

Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and their evaluation as L-selectin inhibitors

• Joana Salta,
• Jens Dernedde and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2015, 11, 638–646, doi:10.3762/bjoc.11.72

• Platz 1, D-13353 Berlin, Germany 10.3762/bjoc.11.72 Abstract In this article a series of divalent and trivalent carbohydrate mimetics on the basis of an enantiopure aminopyran and of serinol is described. These aminopolyols are connected by amide bonds to carboxylic acid derived spacer units either by

• compounds could not be tested as L-selectin inhibitor by SPR due to their insolubility in water, nevertheless, a divalent and a trivalent amide showed surprisingly good activities with IC50 values in the low micromolar range. Keywords: aminopolyols; carbohydrate mimetics; carboxylic acid amides; inhibition

• ; multivalency; selectins; sulfation; Introduction In a series of publications [1][2][3][4][5][6] our group reported on the syntheses of carbohydrate mimetics [7][8][9][10][11] that are based on aminopyrans, aminooxepanes or other aminopolyols. These compounds and their conjugates were prepared to be examined

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

• Maja Kandziora Hans-Ulrich Reissig Freie Universität Berlin, Institut für Chemie und Biochemie, Takustraße 3, D-14195 Berlin, Germany 10.3762/bjoc.10.182 Abstract An approach to β-D-2-aminotalose- and β-D-2-aminoidose-configured carbohydrate mimetics bearing a phenyl substituent is described

• compounds with potential biological activity. In order to achieve this goal we investigated the synthesis of divalent compounds of general structure 1 and their monovalent analogues 2 (Scheme 1). Structurally similar aminopyrans without aryl groups have intensively been studied as carbohydrate mimetics in

• synthesis of divalent compounds 1 with p-terphenyl spacers and of β-D-2-aminotalose- or β-D-2-aminoidose-configured carbohydrate mimetics 2 (Scheme 1). These novel carbohydrate mimetics represent unique structures, combining the features of C-aryl-glycosides and aminosugars. The p-bromophenyl-substituted

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

• mimetics, where several sugar ligands are attached to a non-natural scaffold. Glycopolymers where natural sugar ligands are presented along a synthetic polymer chain are an emerging class of carbohydrate mimetics [5]. Such glycopolymers offer great potential for various biotechnological and biomedical

• affinity carbohydrate ligands by displaying several monosaccharides/oligosaccharides on a protein scaffold or through a patch of lipids. This is known as the glycocluster effect or the multivalent presentation of sugar ligands [3][4]. This strategy can also be employed for the synthesis of carbohydrate

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

• Léa Bouché,
• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 213–223, doi:10.3762/bjoc.10.17

• Lea Bouche Maja Kandziora Hans-Ulrich Reissig Freie Universität Berlin, Institut für Chemie und Biochemie, Takustrasse 3, D-14195 Berlin, Germany 10.3762/bjoc.10.17 Abstract New compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from

• crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics. Keywords: aminooxepanes; carbohydrate mimetics; hydrogenolyses; Lewis acid-induced; lithiated allenes; nitrones

• ; 1,2-oxazines; rearrangements; reductions; Introduction Since carbohydrates play a crucial role in biochemistry, compounds mimicking their structure and/or function (carbohydrate mimetics) have attracted great attention in academic research and in drug development [1][2][3]. These mimetics should not

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• % inhibition of adhesion was observed (data not shown). Moitessier et al. [23] synthesized a combinatorial library of carbohydrate mimetics, based on xylose, as inhibitors of the integrins αIIbβ3 and αvβ3 and blocked binding to the natural ligand RGD, as reviewed by Gruner et al. [24]. Gottschalk and Kessler

Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• , modified mono- or disaccharides have come into the focus of medicinal chemists [8][9]. An important class of carbohydrate mimetics are the C-glycosides [10][11][12][13]. In such compounds the oxygen of the O-glycosidic bond is substituted by a methylene unit rendering them stable to enzymatic degradation

• Suzuki–Miyaura coupling with iodoglucals 6 to yield aliphatic C-glycosides [19]. This method impressively demonstrates the power of the Suzuki–Miyaura coupling in the formation of C(sp2)–C(sp3) bonds for the preparation of carbohydrate mimetics. Friesen and co-workers reported on a synthesis of aryl-C

Addition of lithiated enol ethers to nitrones and subsequent Lewis acid induced cyclizations to enantiopure 3,6-dihydro-2H-pyrans – an approach to carbohydrate mimetics

• Fabian Pfrengle and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 75, doi:10.3762/bjoc.6.75

• dihydroxylation or bromination. Bicyclic enol ether 19 was oxidatively cleaved to provide the highly functionalized ten-membered ring lactone 20. The synthesized enantiopure aminopyrans 24, 26, 28 and 30 can be regarded as carbohydrate mimetics. Trimeric versions of 24 and 28 were constructed via their attachment

• to a tricarboxylic acid core. Keywords: aminopyrans; carbohydrate mimetics; Lewis acids; lithiated enol ethers; nitrones; oxidative cleavage; stereodivergent synthesis; Introduction The pyran structural motif can be found in numerous bioactive natural products. Possible strategies towards their

• ketones. This strategy allowed a simple access to unusual carbohydrates with C2-branched 4-amino sugar units and related carbohydrate mimetics [3][4][5][6][7]. Moreover, pursuing a similar strategy, we described the stereocontrolled preparation of 3,6-dihydro-2H-pyrans D as precursors for the synthesis of

(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

• , much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

• Latif Kelebekli,
• Yunus Kara and
• Murat Celik

Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15

• of carbohydrate mimetics, which can be potent inhibitors of glycosidase (1–4) [11][12][13][14][15][16], we have developed a method for rapid entry to these compounds. Antibiotics containing an aminocyclitol unit have stimulated the development of synthetic methodologies [16] in the search for