Copper‐Catalyzed Azide–Alkyne Cycloaddition: Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles

Spiteri, Christian; Moses, John E.

doi:10.1002/anie.200905322

Cited by 218 publications

(41 citation statements)

References 32 publications

(13 reference statements)

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“…To confirm the results of mass spectrometry analysis, the levels of core-6 fucosylation were further probed with azido fucose using recombinant human FUT8. The incorporated azido fucose was then conjugated to a biotin residue via a click chemistry reaction [19,20], and detected with streptavidin-conjugated horse radish peroxidase [21,22]. As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Core-6 fucose and the oligomerization of the 1918 pandemic influenza viral neuraminidase

Zhou

Ethen

et al. 2016

Biochemical and Biophysical Research Communications

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The 1918 H1N1 influenza virus was responsible for one of the most deadly pandemics in human history. Yet to date, the structure component responsible for its virulence is still a mystery. In order to search for such a component, the neuraminidase (NA) antigen of the virus was expressed, which led to the discovery of an active form (tetramer) and an inactive form (dimer and monomer) of the protein due to different glycosylation. In this report, the N-glycans from both forms were released and characterized by mass spectrometry. It was found that the glycans from the active form had 26% core-6 fucosylated, while the glycans from the inactive form had 82% core-6 fucosylated. Even more surprisingly, the stalk region of the active form was almost completely devoid of core-6-linked fucose. These findings were further supported by the results obtained from in vitro incorporation of azido fucose and 3H-labeled fucose using core-6 fucosyltransferase, FUT8. In addition, the incorporation of fucose did not change the enzymatic activity of the active form, implying that core-6 fucose is not directly involved in the enzymatic activity. It is postulated that core-6 fucose prohibits the oligomerization and subsequent activation of the enzyme.

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Section: Resultsmentioning

confidence: 99%

Core-6 fucose and the oligomerization of the 1918 pandemic influenza viral neuraminidase

Zhou

Ethen

et al. 2016

Biochemical and Biophysical Research Communications

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“…To conjugate the aptamer to the oligopeptide SAM using the azide-alkyne click chemistry reaction2021, the alkyne was coupled to the hydroxyl group of 5′ thymine of the aptamer, using the alkyne-modifier serinol phosphoramidite (Glen Research, USA), and the NH 2 of the K (Lys) at the C-terminus was replaced with an azide (-N 3 ). The oligopeptides with and without azide groups (peptide-N 3 and peptide-COOH) were mixed in an aqueous solution at a ratio of 1:9, of which drops were then placed on a gold-coated glass substrate.…”

Section: Resultsmentioning

confidence: 99%

“…Since the oligopeptides contain cysteine at the N-terminal and the alternating zwitterionic KE sequence at the C-terminal, the oligopeptides chemically adsorb onto the gold substrate via gold-thiol bonding and form a dense self-assembled monolayer (SAM) by electrostatic interactions. After washing with phosphate-buffered saline (PBS), the layer was further modified with an aptamer, 5′-alkyne-TAACTCAATAAGCTAGGTGGGTGGGGGACACTACTCGGGGGTGGTTGGGT-3′ (BEX, Japan) through azide-alkyne click chemistry2021 by placing a drop of 0.3 μM aptamer solution (H 2 O:t-BuOH, 2:1) containing 1.8 mol% CuSO 4 and 8 mol% sodium ascorbate on the substrate and incubating for 8 h at room temperature. Note that the aptamer sequence was previously designed using cell-SELEX for the selection of Hep G2 cells from normal human hepatocytes18.…”

Section: Methodsmentioning

confidence: 99%

Catch-and-Release of Target Cells Using Aptamer-Conjugated Electroactive Zwitterionic Oligopeptide SAM

Enomoto

Kageyama

Osaki

et al. 2017

Sci Rep

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Nucleic acid aptamers possess attractive features such as specific molecular recognition, high-affinity binding, and rapid acquisition and replication, which could be feasible components for separating specific cells from other cell types. This study demonstrates that aptamers conjugated to an oligopeptide self-assembled monolayer (SAM) can be used to selectively trap human hepatic cancer cells from cell mixtures containing normal human hepatocytes or human fibroblasts. Molecular dynamics calculations have been performed to understand how the configurations of the aptamers are related to the experimental results of selective cell capture. We further demonstrate that the captured hepatic cancer cells can be detached and collected along with electrochemical desorption of the oligopeptide SAM, and by repeating these catch-and-release processes, target cells can be enriched. This combination of capture with aptamers and detachment with electrochemical reactions is a promising tool in various research fields ranging from basic cancer research to tissue engineering applications.

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“…We consider that the catalytic cycle of this reaction would be similar to that for the reaction of 1-iodoalkynes [21,33] and 1-bismuthanoalkynes [24] with organic azides. A possible mechanism of the present Cu-catalyzed cycloaddition is shown in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

“…There are many reports of CuAACs by using terminal alkynes (including metal acetylides) [4–20]. But the use of internal alkynes in CuAACs for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles is a more challenging area because of the difficulty in regiocontrol based on the increased steric hindrance [21–22]. A regioselective CuAAC synthesis of fully substituted 1,2,3-triazoles having group 15 (P, Bi) elements as substituents at the C-5 position was recently attempted.…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

Yamada¹,

Matsumura²,

Uchida³

et al. 2016

Beilstein J. Org. Chem.

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SummaryTrisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I2, and NOBF4 afforded 1-benzyl-4-phenyltriazole, 1-benzyl-5-iodo-4-phenyltriazole, and a pentavalent organoantimony compound, respectively.

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Copper‐Catalyzed Azide–Alkyne Cycloaddition: Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles

Cited by 218 publications

References 32 publications

Core-6 fucose and the oligomerization of the 1918 pandemic influenza viral neuraminidase

Core-6 fucose and the oligomerization of the 1918 pandemic influenza viral neuraminidase

Catch-and-Release of Target Cells Using Aptamer-Conjugated Electroactive Zwitterionic Oligopeptide SAM

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

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