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Click Chemistry

The term "click chemistry" was introduced by K. Barry Sharpless et al. and denotes the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links. Their Review in Angewandte Chemie in 2001 still ranks among the most accessed online articles in the journal.

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Recent Articles

Characterisation of Photoaffinity-Based Chemical Probes by Fluorescence Imaging and Native-State Mass Spectrometry

Characterisation of Photoaffinity‐Based Chemical Probes by Fluorescence Imaging and Native‐State Mass Spectrometry

Chemical probe structure–activity relationships: Chemical probes are small-molecule reagents used by researchers for labelling and detection of biomolecules. We demonstrate that a combination of in-gel fluorescence with native state mass spectrometry enables detailed characterisation of photoaffinity labelling (PAL) probe–protein interactions to establish probe structure–activity relationships.

[Full Paper]
Kanae Teruya, Gregory M. Rankin, Panagiotis K. Chrysanthopoulos, Kathryn F. Tonissen, Sally-Ann Poulsen
ChemBioChem, March 22, 2017, https://doi.org/10.1002/cbic.201600598 Read article

Synthesis and Self-Assembly of Amphiphilic Block Copolymers from Biobased Hydroxypropyl Methyl Cellulose and Poly(L-lactide)

Synthesis and Self‐Assembly of Amphiphilic Block Copolymers from Biobased Hydroxypropyl Methyl Cellulose and Poly(L‐lactide)

Hydroxypropyl methyl cellulose-block-poly( l-lactide) (HPMC-b-PLLA) diblock copolymers are synthesized via UV-initiated thiol-ene click reaction of thiol-terminated HPMC and allyl-terminated PLLA. The amphiphilic copolymers are able to self-assemble in water, yielding micelles of 50–100 nm. The copolymers exhibit a thermoresponsive behavior with a lower critical solution temperature around 80 °C.

[Full Paper]
Jielin Wang, Marleny Caceres, Suming Li, André Deratani
Macromol. Chem. Phys., March 17, 2017, https://doi.org/10.1002/macp.201600558 Read article

Glass–Metal Adhesive Polymers from Copper(I)-Catalyzed Azide–Alkyne Cycloaddition

Glass–Metal Adhesive Polymers from Copper(I)‐Catalyzed Azide–Alkyne Cycloaddition

The preparation of a library of hyperbranched polytriazole networks via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) for the adhesion between metal and glass surfaces is reported. The triazole groups constitute stable linkages in the adhesive matrix, bind noncovalently to the surfaces, and coordinates Cu(I) ions to facilitate further CuAAC reactions.

[Full Paper]
Yeimy M. Martínez-Triana, Rory Whelan, M. G. Finn, David Díaz Díaz
Macromol. Chem. Phys., March 15, 2017, https://doi.org/10.1002/macp.201600579 Read article

Direct Intracellular Delivery of Cell-Impermeable Probes of Protein Glycosylation by Using Nanostraws

Direct Intracellular Delivery of Cell‐Impermeable Probes of Protein Glycosylation by Using Nanostraws

Azidosugar interjection: Substrates for protein glycosylation were directly delivered into the cell cytoplasm through nanoscale conduits on a nanostraw platform. This technique can be used to introduce bulky, charged, and cell-impermeable azidosugar substrates and reaction intermediates into the glycosylation pathway for subsequent labeling with click chemistry probes.

[Communication]
Alexander M. Xu, Derek S. Wang, Peyton Shieh, Yuhong Cao, Nicholas A. Melosh
ChemBioChem, March 14, 2017, https://doi.org/10.1002/cbic.201600689 Read article

Electrochemiluminescence of a Vinyl-Functionalized Ruthenium Complex and Its Monolayer Formed through the Photoinduced Thiol-Ene Click Reaction

Electrochemiluminescence of a Vinyl‐Functionalized Ruthenium Complex and Its Monolayer Formed through the Photoinduced Thiol‐Ene Click Reaction

Ready to react: Electrochemiluminescence (ECL) generated from vinyl-functionalized bipyridine ruthenium complex, [Ru(bpy)2(dvbpy)]2+, is studied by using an ECL spooling technique. Its monolayer immobilized on an ITO electrode is also prepared through the thiol-ene click reaction. This solid-state ECL sensor exhibits good ECL stability and a large linear range for the model analysis of common amine species, such as TPrA.

[Article]
Weiliang Guo, Zhiyuan Cao, Yanhuan Liu, Bin Su
ChemElectroChem, March 06, 2017, https://doi.org/10.1002/celc.201600905 Read article

Versatile Two-Step Functionalization of Nanocarbons: Grafting of Propargylic Groups and Click Post-Functionalization

Versatile Two‐Step Functionalization of Nanocarbons: Grafting of Propargylic Groups and Click Post‐Functionalization

Hard graft: The efficient grafting of alkynyl groups through a two-step nucleophilic addition and propargylic capture reaction is proposed. The attached alkyne moieties are further reacted with azide derivatives through copper-catalyzed alkyne–azide cycloaddition (CuAAC).

[Communication]
Antonin Desmecht, Sophie Hermans, Olivier Riant
ChemistryOpen, February 28, 2017, https://doi.org/10.1002/open.201600170 Read article

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