Table of contents

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Homemade chemists p687

Michelle Francl


Michelle Francl wonders if home labs make (better) chemists.

Subject term: General chemistry



Blogroll: But is it art? p691

See Arr Oh



News and Views

Medicinal chemistry: Forcing an enemy into the open pp692 - 693

Christian Melander & David M. Margolis


A series of highly active, simplified analogues of the natural product bryostatin have been prepared. They offer an improved approach for the activation of latent HIV that could, in combination with current state-of-the-art antiretroviral therapy, offer hope for eventual eradication of the infection.

Subject terms: Medicinal chemistry | Synthesis

See also: Article by DeChristopher et al.

Protein NMR spectroscopy: Hydrogen bonds under pressure pp693 - 695

Gerd Nielsen & Harald Schwalbe


Hydrogen bonds play a key role in defining the folding of proteins and the maintenance of their structure. A high-pressure NMR study of ubiquitin now provides unprecedented detail on the temperature and pressure dependence of its hydrogen-bond network.

Subject terms: Chemical biology | Physical chemistry | Analytical chemistry

See also: Article by Nisius & Grzesiek

Molecular switches: Hydrazones double down on zinc pp695 - 696

Shawn C. Burdette


Molecular engineers have long relied on a single light-driven event or chemical input to induce structural changes in switching systems. By carefully designing two hydrazone-based switches, it has now been shown that a single metal-binding event can trigger a signalling cascade that results in the isomerization of two different molecules.

Subject terms: Organic chemistry | Supramolecular chemistry

See also: Article by Ray et al.

Carbohydrate recognition: A minimalistic approach to binding pp697 - 698

Stefan Kubik


Synthetic receptors with properties resembling those of carbohydrate-binding proteins are known, but they are structurally rather complex. Elaborate structures are, however, not always required to bind carbohydrates in water — much simpler compounds can be just as effective.

Subject terms: Organic chemistry | Supramolecular chemistry

See also: Article by Ke et al.



Design strategies for organic semiconductors beyond the molecular formula pp699 - 704

Zachary B. Henson, Klaus Müllen & Guillermo C. Bazan


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Although the molecular formula gives valuable information on the properties of isolated molecules or conjugated polymers, it fails to accurately predict their collective behaviour in the solid state. This Perspective highlights the importance of organization across multiple length scales on the optical and electronic properties of organic semiconductors, and how device performances poorly reflect the capabilities of a given material.

Subject terms: Materials chemistry | Supramolecular chemistry | Polymer chemistry



Designed, synthetically accessible bryostatin analogues potently induce activation of latent HIV reservoirs in vitro pp705 - 710

Brian A. DeChristopher, Brian A. Loy, Matthew D. Marsden, Adam J. Schrier, Jerome A. Zack & Paul A. Wender


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Simplified bryostatin analogues are shown to potently induce latent HIV expression in vitro. These analogues display comparable or better potency when compared with bryostatin. Moreover, they are up to 1,000-fold more potent in inducing latent HIV expression than prostratin, the current lead preclinical candidate.

Subject terms: Synthesis | Medicinal chemistry

See also: News and Views by Melander & Margolis

Key stabilizing elements of protein structure identified through pressure and temperature perturbation of its hydrogen bond network pp711 - 717

Lydia Nisius & Stephan Grzesiek


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The pressure- and temperature-dependent changes of various hydrogen bonds within ubiquitin have been determined at very high resolution using NMR H-bond scalar couplings. The measured perturbations show a correlation with the sequence separation between donor and acceptor residues, and indicate that certain topologically crucial H-bonds are specifically stabilized.

Subject terms: Chemical biology | Physical chemistry | Analytical chemistry

See also: News and Views by Nielsen & Schwalbe

A simple and accessible synthetic lectin for glucose recognition and sensing pp718 - 723

Chenfeng Ke, Harry Destecroix, Matthew P. Crump & Anthony P. Davis


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Selective carbohydrate binding is a difficult task, usually accomplished by proteins (lectins) or complex synthetic analogues. It has now been achieved by a remarkably simple compound, accessible in just five steps from commercially available materials. This new receptor is highly selective for all-equatorial carbohydrates, and may be used to sense glucose through changes in anthracene fluorescence.

Subject terms: Organic chemistry | Supramolecular chemistry

See also: News and Views by Kubik

Understanding and controlling the substrate effect on graphene electron-transfer chemistry via reactivity imprint lithography pp724 - 732

Qing Hua Wang, Zhong Jin, Ki Kang Kim, Andrew J. Hilmer, Geraldine L. C. Paulus, Chih-Jen Shih, Moon-Ho Ham, Javier D. Sanchez-Yamagishi, Kenji Watanabe, Takashi Taniguchi, Jing Kong, Pablo Jarillo-Herrero & Michael S. Strano


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The chemical modification of graphene is important for its use in many applications. Now it is shown that the reactivity of graphene towards covalent modification varies widely depending on its underlying support substrate, and that the substrate can be patterned to induce spatial control of chemical reactions in graphene.

Subject term: Nanotechnology

Highly enantioselective trapping of zwitterionic intermediates by imines pp733 - 738

Huang Qiu, Ming Li, Li-Qin Jiang, Feng-Ping Lv, Li Zan, Chang-Wei Zhai, Michael P. Doyle & Wen-Hao Hu


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Reactions with unstable and highly reactive zwitterionic intermediates generated in transition-metal-catalysed processes provide new opportunities for molecular constructions. Here imines, activated by chiral organocatalysts, have been employed to trap the zwitterionic intermediates to give polyfunctionalized indole and oxindole derivatives in a single step with excellent diastereoselectivity and enantioselectivity.

Subject terms: Catalysis | Synthesis

In situ surface coverage analysis of RuO2-catalysed HCl oxidation reveals the entropic origin of compensation in heterogeneous catalysis pp739 - 745

Detre Teschner, Gerard Novell-Leruth, Ramzi Farra, Axel Knop-Gericke, Robert Schlögl, László Szentmiklósi, Miguel González Hevia, Hary Soerijanto, Reinhard Schomäcker, Javier Pérez-Ramírez & Núria López


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In heterogeneous catalytic processes the Arrhenius parameters are often found to be interrelated (compensation phenomenon). Using state-of-the-art experiments and density functional theory, the origin of compensation is studied. A similar dependence on the rate-limiting surface-coverage term is found for both apparent activation energy and prefactor terms, which can be translated into surface configurational entropy contributions.

Subject terms: Catalysis | Physical chemistry | Theoretical chemistry

A quantitative model for the transcription of 2D patterns into functional 3D architectures pp746 - 750

Edvinas Orentas, Marco Lista, Nai-Ti Lin, Naomi Sakai & Stefan Matile


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The self-sorting of molecular building blocks should allow 2D surface patterns to be transcribed into 3D functional materials. Here, a non-empirical approach to the templated synthesis of supramolecular architectures on surfaces is reported, starting with a theoretical model and followed by comprehensive experimental validation, including direct evidence for functional relevance of the produced materials.

Subject terms: Supramolecular chemistry | Materials chemistry

Anion-induced reconstitution of a self-assembling system to express a chloride-binding Co10L15 pentagonal prism pp751 - 756

Imogen A. Riddell, Maarten M. J. Smulders, Jack K. Clegg, Yana R. Hristova, Boris Breiner, John D. Thoburn & Jonathan R. Nitschke


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A coordination cage has been prepared that self-assembles through second-order templation. Peripheral perchlorate or hexafluorophosphate template anions direct the formation of a hollow prism whose central pocket was able to bind a small anionic guest such as halide or azide, in a manner reminiscent to signal transduction in biological systems.

Subject term: Supramolecular chemistry

A switching cascade of hydrazone-based rotary switches through coordination-coupled proton relays pp757 - 762

Debdas Ray, Justin T. Foy, Russell P. Hughes & Ivan Aprahamian


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Metal cations play an important role in biological proton relays by modulating the pKa values of surrounding amino acids. This effect has now been used to induce the isomerization of two hydrazone switches using a single input. It is found that a combination of electrostatic repulsion and conformational changes are required for the proton relay to take place.

Subject terms: Organic chemistry | Supramolecular chemistry

See also: News and Views by Burdette


In Your Element

Reactions coupled to palladium p764

Matthew Hartings


You would be forgiven if you thought the most important element in an organic transformation was carbon. Matthew Hartings argues that, for just over half a century in many of chemistry's most renowned organic reactions, it has actually been palladium.