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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

Polylutidines: Multifunctional Surfaces through Vapor-Based Polymerization of Substituted Pyridinophanes

Polylutidines: Multifunctional Surfaces through Vapor‐Based Polymerization of Substituted Pyridinophanes

Coat of many nitrogens! Chemical vapor deposition based polymers have been widely used as biomedical interfaces, but all of these coatings are restricted to simple all-carbon backbones. For the first time, a class of functionalized lutidine polymers has been prepared by chemical vapor deposition (see figure). This reactive coating opens new perspectives for the design of new cell biomedical applications.

[Full Paper]
Florence Bally-Le Gall, Christoph Hussal, Joshua Kramer, Kenneth Cheng, Ramya Kumar, Thomas Eyster, Amy Baek, Vanessa Trouillet, Martin Nieger, Stefan Bräse, Joerg Lahann
Chem. Eur. J., August 16, 2017, https://doi.org/10.1002/chem.201700901 Read article

Cyclisation To Form Small, Medium and Large Rings by Use of Catalysed and Uncatalysed Azide–Alkyne Cycloadditions (AACs)

Cyclisation To Form Small, Medium and Large Rings by Use of Catalysed and Uncatalysed Azide–Alkyne Cycloadditions (AACs)

This microreview briefly summarises recent developments in the cyclisation to form small, medium and large rings (five to 30 or more members) by way of both catalysed and uncatalysed azide–alkyne cycloaddition (AAC). In addition, we present useful strategies for overcoming common problems encountered in these reactions.

[Microreview]
Thomas M. A. Barlow, Dirk Tourwé, Steven Ballet
Eur. J. Org. Chem., August 15, 2017, https://doi.org/10.1002/ejoc.201700521 Read article

Click Chemistry in Functional Aliphatic Polycarbonates

Click Chemistry in Functional Aliphatic Polycarbonates

Click chemistry is a critical methodology in synthesizing functional aliphatic polycarbonates in the past two decades. In this Feature Article, six categories of click reactions (alkyne-azide reaction, thiol-ene reaction, Michael addition, epoxy-amine/thiol reaction, Diels-Alder reaction, and imine formation) that have been afforded for further post-polymerization modification of polycarbonates are reviewed. The features and limitations of each reaction are also summarized.

[Feature Article]
Yu Dai, Xiaojin Zhang, Fan Xia
Macromol. Rapid Commun., August 10, 2017, https://doi.org/10.1002/marc.201700357 Read article

Irreversible Protein Labeling by Paal–Knorr Conjugation

Irreversible Protein Labeling by Paal–Knorr Conjugation

Labeling lysines: Recent advances toward a suite of bioorthogonal chemical reactions have profoundly enhanced the tools available to biochemists to study proteins and other biomolecules. Here, we describe the use of the Paal–Knorr reaction to fluorescently label proteins. The described procedures operate without reagents, catalysts, or organic solvents, as needed for a biocompatible method.

[Communication]
Ramesh Dasari, James J. La Clair, Alexander Kornienko
ChemBioChem, August 10, 2017, https://doi.org/10.1002/cbic.201700210 Read article

Specific Binding of Liposomal Nanoparticles through Inverse Electron-Demand Diels–Alder Click Chemistry

Specific Binding of Liposomal Nanoparticles through Inverse Electron‐Demand Diels–Alder Click Chemistry

Clearing through clicking: Development of an 89Zr-labeled trans-cyclooctene-modified liposomal nanoparticle and a tetrazine-modified CoCrMo alloy (Tz-PDA@CoCrMo). First investigations utilizing a new platform technology to specifically bind liposomal radiopharmaceuticals through the inverse electron-demand Diels–Alder click.

[Communication]
Christian Brand, Pasquale Iacono, Carlos Pérez-Medina, Willem J. M. Mulder, Moritz F. Kircher, Thomas Reiner
ChemistryOpen, August 07, 2017, https://doi.org/10.1002/open.201700105 Read article

Modulation of Mitochondriotropic Properties of Cyanine Dyes by in Organello Copper-Free Click Reaction

Modulation of Mitochondriotropic Properties of Cyanine Dyes by in Organello Copper‐Free Click Reaction

Mitochondrial meeting point: Cyanine (Cy) dyes show a general propensity to localize in polarized mitochondria. This mitochondriotropism is used to perform a copper-free click reaction in the mitochondria of living cells. A Cy3–Cy5 conjugate shows enhanced retention in mitochondria, compared with the starting compounds. This enhancement of a favorable property can be achieved by synthesis in organello, but not outside mitochondria.

[Communication]
Inka Negwer, Markus Hirsch, Stefka Kaloyanova, Tom Brown, Kalina Peneva, Hans-Jürgen Butt, Kaloian Koynov, Mark Helm
ChemBioChem, July 31, 2017, https://doi.org/10.1002/cbic.201700286 Read article

Synthetic Nucleic Acid Analogues in Gene Therapy: An Update for Peptide–Oligonucleotide Conjugates

Synthetic Nucleic Acid Analogues in Gene Therapy: An Update for Peptide–Oligonucleotide Conjugates

Greater than the sum of its parts: The field of therapeutic oligonucleotides is growing constantly, which provides exciting opportunities in life sciences and clinical research. Recent developments in the synthesis and biological properties of conjugates formed by oligonucleotides and peptides is described, with special attention to the delivery of nucleic acid therapeutics.

[Review]
Maria Taskova, Anna Mantsiou, Kira Astakhova
ChemBioChem, July 24, 2017, https://doi.org/10.1002/cbic.201700229 Read article

Dendrimer-Based Signal Amplification of Click-Labelled DNA in Situ

Dendrimer‐Based Signal Amplification of Click‐Labelled DNA in Situ

Finding a needle in a haystack: A new method to detect proliferating cells in situ by using multiple consecutive click reactions with dendrimeric molecules and clickable dyes is presented. These assays have outstanding sensitivities; signal intensities and signal-to-noise ratios are far better than those obtained by techniques that are currently available. EdU=ethinyl-dU.

[Communication]
Nada Raddaoui, Samuele Stazzoni, Leonhard Möckl, Bastien Viverge, Florian Geiger, Hanna Engelke, Christoph Bräuchle, Thomas Carell
ChemBioChem, July 24, 2017, https://doi.org/10.1002/cbic.201700209 Read article

In-Situ Generated and Premade 1-Copper(I) Alkynes in Cycloadditions

In‐Situ Generated and Premade 1‐Copper(I) Alkynes in Cycloadditions

Based on the investigation of the references and our works on CuAAC reaction, we found the difference and conversion between the in-situ generated and the premade 1-copper(I) alkynes. Finally, the novel carboxylic acid-promoted CuAAC strategy was developed, which has been proven to be the most convenient and highly efficient CuAAC method to date. Furthermore, the novel function of the premade 1-copper(I) alkynes as excellent dipolarophiles was first disclosed and applied. In this article, a series of works reported by our group for the in-situ generated and the premade 1-copper(I) alkynes in cycloadditions are reviewed.

[Personal Account]
Xinyan Wang, Xingyong Wang, Xuesong Wang, Jianlan Zhang, Chulong Liu, Yuefei Hu
Chem. Rec., June 22, 2017, https://doi.org/10.1002/tcr.201700011 Read article

Efficient Polymer-Polymer Conjugation via Thiol-ene Click Reaction

Efficient Polymer‐Polymer Conjugation via Thiol‐ene Click Reaction

Considerations particular to radical thiol-ene conjugation of polymers are reviewed. Mitigation of characteristic challenges is discussed and the successful coupling of polymers via radical thiol-ene reaction is demonstrated. Both functional group and initiator determine the extent of successful polymer-polmyer coupling.

[Trend]
Benjamin D. Fairbanks, Dillon M. Love, Christopher N. Bowman
Macromol. Chem. Phys., June 08, 2017, https://doi.org/10.1002/macp.201700073 Read article

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