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Search for "azide–alkyne" in Full Text gives 131 result(s) in Beilstein Journal of Organic Chemistry.

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

  • Shaojin Gu,
  • Jiehao Du,
  • Jingjing Huang,
  • Huan Xia,
  • Ling Yang,
  • Weilin Xu and
  • Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

Graphical Abstract
  • imidazolium backbone and N substituents. The copper–NHC complexes tested are highly active for the Cu-catalyzed azidealkyne cycloaddition (CuAAC) reaction in an air atmosphere at room temperature in a CH3CN solution. Complex 4 is the most efficient catalyst among these polynuclear complexes in an air
  • Inspired by the catalytic activity of Cu(I) species supported by NHC ligand in Cu-catalyzed azidealkyne cycloaddition (CuAAC) reaction under mild conditions, copper complexes 2–6 were investigated in the CuAAC reaction of azide and phenylacetylene. Firstly, we compared the catalytic activity of different
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Published 03 May 2016

Creating molecular macrocycles for anion recognition

  • Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

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  • house is just as satisfying as that of a new molecule and often takes the same amount of time (left: Franck Boston copyright 123RF.com). Timeline of anion-binding macrocycles. Click chemistry’s copper-catalyzed azidealkyne cycloaddition (CuAAC) forms 1,2,3-triazoles that stabilize anions by CH hydrogen
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Published 31 Mar 2016

Enabling technologies and green processes in cyclodextrin chemistry

  • Giancarlo Cravotto,
  • Marina Caporaso,
  • Laszlo Jicsinszky and
  • Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

Graphical Abstract
  • is the Cu(0)-catalysed azidealkyne cycloaddition (CuAAC) that can be further enhanced by simultaneous US/MW irradiation [18]. The formation of triazole-substituted CDs has been investigated by US irradiation and products can be synthesized in 2–4 hours (Scheme 2) [19]. Scondo et al. have reported a
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Published 15 Feb 2016

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

  • Sophie Letort,
  • Sébastien Balieu,
  • William Erb,
  • Géraldine Gouhier and
  • François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

Graphical Abstract
  • a cooper(I)-catalyzed azidealkyne cycloaddition between the 2’-azido-β-CD 31 and the alkyne derivatives 22a,b to access the corresponding monosubstituted CD 32a,b [76]. Synthesis of 3-monosubstituted β-CD derivatives: As the facial position of the reactive groups might modify the catalytic
  • partially-protected 2,6-dimethyl-β-CD (Scheme 7) [88]. Finally, CDs bearing an oxime (36 and 39a) or a hydroxamic acid (39b) group in position 3 were prepared as previously described via an azidealkyne cycloaddition (Scheme 7) [76][80]. Synthesis of difunctionalized β-CD derivatives: As the hydrolytic
  • disulfonylimidazole 42 to access a key intermediate easily converted to the corresponding di-2,3-mannoepoxido compound 43 (Scheme 8) [89]. The 3A,3B-diazido-3A,3B-dideoxy-bis(altro)-β-cyclodextrin 44 was then obtained by reaction of 43 with sodium azide and a copper(I)-catalyzed azidealkyne cycloaddition finally
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Published 05 Feb 2016

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

Graphical Abstract
  • chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human
  • multimerization of compound ent-1 with the aim of studying its inhibitory activity when the molecule decorates a multivalent scaffold. Herein we report the synthesis of a tetra- and a nonavalent polyhydroxypiperidine iminosugar, by exploiting the CuI-catalyzed azide-alkyne cycloadditions (CuAAC) [29][30][31][32
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Published 16 Dec 2015

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

  • Zhan-Jiang Zheng,
  • Ding Wang,
  • Zheng Xu and
  • Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

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  • Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, P. R. China 10.3762/bjoc.11.276 Abstract The Cu(I)-catalyzed azide-alkyne cycloaddition reaction, also known as click chemistry, has become a useful tool for the facile formation of 1,2,3-triazoles
  • investigated and recognized as an epoch-making progress in organic synthesis and green chemistry [11][12][13][14][15]. After many years of research, it was proven that the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC reaction) could be performed under various conditions according to the need of click
  • - and para-ethynylaniline, where both of the substrates worked well and the desired bistriazoles 34 could be obtained by a simple trituration and filtration procedure in good yield. The strain-promoted azide-alkyne cycloaddition (SPAAC) reaction could be well-performed without a Cu(І) catalyst. Such
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Published 11 Dec 2015

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

  • Nicolas Desbois,
  • Sandrine Pacquelet,
  • Adrien Dubois,
  • Clément Michelin and
  • Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

Graphical Abstract
  • -like macrocycle on the other side, have been easily linked by microwave azidealkyne 1,3-dipolar cycloaddition. The preliminary relaxivity study of these heterobimetallic complexes was also investigated for potential MRI applications. Results and Discussion We first wish to report a “library” of azido
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Published 17 Nov 2015

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

  • Mohamed Ramadan El Sayed Aly,
  • Hosam Ali Saad and
  • Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

Graphical Abstract
  • corresponding to the exact molecular weight of each derivative supported these azidealkyne cycloadditions. The second set of cholesterol conjugates (Scheme 2 and Scheme 3) was prepared by CuAAC of (3β)-3-(prop-2-yn-1-yloxy)cholest-5-ene (10) with azidoalcanols 9a,b [24] and 3β-azidocholest-5-ene (3). These
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Published 16 Oct 2015

Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition

  • Zachary L. Palchak,
  • Paula T. Nguyen and
  • Catharine H. Larsen

Beilstein J. Org. Chem. 2015, 11, 1425–1433, doi:10.3762/bjoc.11.154

Graphical Abstract
  • ; copper catalysis; multicomponent reactions; tetrasubstituted carbon; triazole; Introduction 1,2,3-Triazoles demonstrate wide spread application in biological systems and drug development [1][2][3][4][5][6][7][8][9][10][11][12]. Copper-catalyzed azidealkyne cycloadditions (CuAAC) regioselectively
  • second portion of the sequence in Scheme 1: a tandem deprotection–cycloaddition of tetrasubstituted TIPS-protected propargylamines 4 that would allow them to react in situ with various azides 5 to give hindered triazoles 6. As a copper(I) catalyst is required for azidealkyne cycloaddition, the
  • -deprotection with azidealkyne cycloaddition, producing hindered triazoles in 6 hours. This tandem reaction was optimal with a copper(II) triflate and sodium ascorbate (NaAsc) as a mild reductant. The outcome that copper(II) triflate provides the highest yields for the one-pot deprotection/click reaction was
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Published 14 Aug 2015

Selected synthetic strategies to cyclophanes

  • Sambasivarao Kotha,
  • Mukesh E. Shirbhate and
  • Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

Graphical Abstract
  • (Scheme 51). [3 + 2] Cycloaddition (1,3-dipolar cycloaddition/click reaction): In 2010, Raghunathan and co-workers [185] have synthesized a C2-symmetric triazolophane by a copper(I)-catalyzed azide-alkyne cycloaddition, involving a click reaction. The dipropargyl fluorenyl derivative 299 was prepared from
  • ] have reported the synthesis of a glycotriazolophane 309 (carbohydrate–triazole–cyclophane hybrid) from a sugar amino acid via a copper-catalyzed azide-alkyne cycloaddition sequence. An aminosugar acid was identified as a useful building block to generate cyclophanes. Thus, the treatment of 304 with
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Published 29 Jul 2015

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

  • Madhuri V. Shinde,
  • Rohini S. Ople,
  • Ekta Sangtani,
  • Rajesh Gonnade and
  • D. Srinivasa Reddy

Beilstein J. Org. Chem. 2015, 11, 1060–1067, doi:10.3762/bjoc.11.119

Graphical Abstract
  • Carell et al. in 2007 [40]. The work of Aubé on AAC (azidealkyne cycloaddition) chemistry also gives a good indication that equilibrating allylic azide stereoisomers can selectively participate in reactions [37][38][39][40][41][42][43][44][45]. In 2000, Aubé et al. proposed a mechanism for the
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Published 23 Jun 2015

Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization

  • Shun Nakano,
  • Akihito Hashidzume and
  • Takahiro Sato

Beilstein J. Org. Chem. 2015, 11, 1037–1042, doi:10.3762/bjoc.11.116

Graphical Abstract
  • . Keywords: 3-azido-1-propyne oligomer; CuAAC polymerization; hydrodynamic radius; methyl iodide; pulse-field-gradient spin-echo NMR; quarternization; Introduction The copper(I)-catalyzed azidealkyne cycloaddition (CuAAC) efficiently yields 1,4-disubstituted-1,2,3-triazole from rather stable azides and
  • Shun Nakano Akihito Hashidzume Takahiro Sato Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan 10.3762/bjoc.11.116 Abstract 3-Azido-1-propyne oligomer (oligoAP) samples, prepared by copper(I)-catalyzed azide
  • alkyne cycloaddition (CuAAC) polymerization, were quarternized quantitatively with methyl iodide in sulfolane at 60 °C to obtain soluble oligomers. The conformation of the quarternized oligoAP in dilute DMSO-d6 solution was examined by pulse-field-gradient spin-echo NMR based on the touched bead model
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Published 18 Jun 2015

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

  • Michaela Mühlberg,
  • Michael G. Hoesl,
  • Christian Kuehne,
  • Jens Dernedde,
  • Nediljko Budisa and
  • Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

Graphical Abstract
  • combines residue-specific incorporation of unnatural amino acids with chemical oxidative aldehyde formation at the N-terminus of a protein. Our approach relies on the selective introduction of two different functional moieties in a protein by mutually orthogonal copper-catalyzed azidealkyne cycloaddition
  • engineer multivalent glycoprotein conjugates, we have used the incorporation of non-canonical amino acids (NCAA) [13] by supplementation based incorporation (SPI) [14][15][16][17] in auxotroph expression systems followed by the chemoselective Cu-catalyzed azidealkyne cycloaddition (CuAAC) to attach
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Published 13 May 2015

Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations

  • Tommaso Pecchioli,
  • Manoj Kumar Muthyala,
  • Rainer Haag and
  • Mathias Christmann

Beilstein J. Org. Chem. 2015, 11, 730–738, doi:10.3762/bjoc.11.83

Graphical Abstract
  • according to well-established protocols [65]. Consequently, we adopted the Sharpless–Fokin modification for the Huisgen azidealkyne cycloaddition [66] to achieve the final immobilization of the modified imidazolidin-4-one onto the hyperbranched polymer and on the G1 dendron [65]. The progress of the
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Published 12 May 2015

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

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  • 12) had marginal impact on the binding suggesting a saturation of binding site occupancy. For the structure with 6 units of maltose on each arm, a KD of 1 μM was measured which is 700-fold more potent (40-fold per sugar) than monovalent maltose. The advent of the copper-catalyzed azidealkyne
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Published 11 May 2015

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

  • Mathieu L. Lepage,
  • Antoine Mirloup,
  • Manon Ripoll,
  • Fabien Stauffert,
  • Anne Bodlenner,
  • Raymond Ziessel and
  • Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

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  • molecular probes and synthesized by way of Cu(I)-catalysed azidealkyne cycloadditions are fluorescent analogues of potent pharmacological chaperones/correctors recently reported in the field of Gaucher disease and cystic fibrosis, two rare genetic diseases caused by protein misfolding. Keywords: BODIPY
  • interest of the pyrene scaffold lies in its rigidity, a property that may favourably impact inhibitory multivalent effects [9][11][16][19]. A convergent approach comprising the attachment of azide-armed iminosugars 4 [11][12] on polyalkyne “clickable” scaffolds 5 and 6 via Cu(I)-catalyzed azidealkyne
  • -methylumbelliferone or other coumarine derivatives has thus to be taken into account during the quantitative analyses of dedicated biological processes. Conclusion We have reported the preparation of multivalent iminosugar clusters based on two fluorescent cores by way of Cu(I)-catalysed azidealkyne cycloadditions
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Published 06 May 2015

Synthesis and surface grafting of a β-cyclodextrin dimer facilitating cooperative inclusion of 2,6-ANS

  • Lars W. Städe,
  • Thorbjørn T. Nielsen,
  • Laurent Duroux,
  • Reinhard Wimmer,
  • Kyoko Shimizu and
  • Kim L. Larsen

Beilstein J. Org. Chem. 2015, 11, 514–523, doi:10.3762/bjoc.11.58

Graphical Abstract
  • to parent β-CD) for the inclusion of lipophilic molecules [5][9]. The extensive research on the topic has generated a vast number of different β-CD-dimer constructs and methods for the synthesis thereof. Of these methods, synthesis by click chemistry (and specifically the copper(I)-catalyzed azide
  • alkyne cycloaddition (CuAAC)) is very attractive [10][11]. CuAAC is known to be selective, proceed fast and produce a high yield under mild conditions. Further, the formed triazole is stable against oxidation, reduction and hydrolysis [10]. Concerning the design of β-CD dimers, it was recently
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Published 21 Apr 2015

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

  • Roberto Romeo,
  • Caterina Carnovale,
  • Salvatore V. Giofrè,
  • Maria A. Chiacchio,
  • Adriana Garozzo,
  • Emanuele Amata,
  • Giovanni Romeo and
  • Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

Graphical Abstract
  • Sharpless [46] (Scheme 1 and Table 1). The click chemistry process, carried out with equimolar amounts of the respective dipolarophiles, afforded in all the cases the corresponding C-5’-triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides 13 and 14 in good yields (79–89%). According to other copper-catalyzed azide
  • alkyne cycloadditions, no traces of 1,5-regioisomers were observed [47][48]. The structure of the obtained compounds was assessed according to 1H NMR, 13C NMR and MS data. In particular, the 1H NMR spectra of 5-methyl-1-[(3RS,5SR)-2-methyl-3-(1H-1,2,3-triazol-1-ylmethyl)isoxazolidin-5-yl]pyrimidine-2,4
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Published 09 Mar 2015

Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

  • Kuppusamy Bharathimohan,
  • Thanasekaran Ponpandian,
  • A. Jafar Ahamed and
  • Nattamai Bhuvanesh

Beilstein J. Org. Chem. 2014, 10, 3031–3037, doi:10.3762/bjoc.10.321

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  • methodology is more convenient to produce the complex polycyclic molecules in a simple way. Keywords: copper(II) acetate; decarboxylative CuAAC; dehydrogenative coupling; fused triazoles; one-pot synthesis; Introduction The copper-catalyzed Huisgen [3 + 2] cycloaddition (or copper-catalyzed azidealkyne
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Published 17 Dec 2014

Organic chemistry on surfaces: Direct cyclopropanation by dihalocarbene addition to vinyl terminated self-assembled monolayers (SAMs)

  • Malgorzata Adamkiewicz,
  • David O’Hagan and
  • Georg Hähner

Beilstein J. Org. Chem. 2014, 10, 2897–2902, doi:10.3762/bjoc.10.307

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  • including azidealkyne cycloadditions [9][10], Diels–Alder reactions [11][12], maleimide–thiol reactions [13], thiol–ene additions [14], and imine/oxime conjugations [15]. In this article we demonstrate that dihalocarbenes can be used to generate dihalocyclopropanes on olefin terminated SAMs. We recently
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Published 05 Dec 2014

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

  • Stefanie Wolfram,
  • Hendryk Würfel,
  • Stefanie H. Habenicht,
  • Christine Lembke,
  • Phillipp Richter,
  • Eckhard Birckner,
  • Rainer Beckert and
  • Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

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  • )-catalyzed azidealkyne cycloaddition (CuAAC) is often considered as the prototypical transformation [7][8][9]. Due to the mild conditions and the use of aqueous solvents it is an efficient tool for bioorthogonal chemistry even inside of living systems [10]. One application of this concept for functional
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Published 23 Oct 2014

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

  • Anne-Katrin Späte,
  • Verena F. Schart,
  • Julia Häfner,
  • Andrea Niederwieser,
  • Thomas U. Mayer and
  • Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

Graphical Abstract
  • bioorthogonal labeling reactions that allow visualization [5][6]. Whereas in the first report on glycan labeling by this approach the ketone–hydrazide ligation was employed [7], later investigations mainly relied on the Staudinger ligation [8] and azidealkyne [3 + 2] cycloaddition (copper-catalyzed [9][10] or
  • fact that it can be orthogonal to the azidealkyne cycloaddition [22][26][27] which allows dual labeling of two different sugars within one experiment [19][21][23][24]. Among the dienophiles mentioned above, strained cyclopropenes have the highest reaction rates for DAinv reactions with tetrazines and
  • by simultaneous DAinv reaction and strain-promoted azidealkyne cycloaddition in a single step [24]. The potential of Ac4ManNCyoc (3) for labeling of sialoglycoconjugates was also recognized by others [30]. Sialic acids are prominently positioned at the outer end of membrane glycoproteins which makes
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Published 22 Sep 2014

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

Graphical Abstract
  • -triazine (2) as a key precursor [37]. The glycosyl units were incorporated via Cu(I)-catalyzed Huisgen cycloaddition with protected or unprotected glycosyl azides. We first investigated the Cu-catalyzed azidealkyne cycloaddition (CuAAC) of acetyl protected β-D-galactopyranosyl azide 3 [38], to tris
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Published 25 Aug 2014

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

  • Silvia Bernardi,
  • Paola Fezzardi,
  • Gabriele Rispoli,
  • Stefania E. Sestito,
  • Francesco Peri,
  • Francesco Sansone and
  • Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

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  • have been widely studied in their scope and limitations [10][31]. In particular, the Huisgen cycloaddition reaction was first applied to a calixarene in 2000 by Santoyo-González [32]. Later on, Marra et al. [33] demonstrated that the copper-catalyzed azidealkyne cycloaddition (CuAAC) [34][35] at room
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Published 23 Jul 2014

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

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  • block AZO. TDS allows for the conjugation of sugar azide ligands via the copper-catalyzed azidealkyne cycloaddition (CuAAC). The synthesis and coupling on solid support of TDS and EDS has been previously described [7][10]. AZO was synthesized via Mills coupling adapting literature protocols [20][21][22
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Published 15 Jul 2014
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