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Nature Chemistry Contents February 2018 Volume 10 Number 2 pp 111 - 244

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Nature Chemistry

Nature Collection: 2017 Nobel Prize in Chemistry 

Nature Research present this Collection of articles celebrating the 2017 Nobel Prize in Chemistry to Jacques Dubochet, Joachim Frank and Richard Henderson, recognised "for developing cryo-electron microscopy for the high-resolution structure determination of biomolecules in solution". 

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February 2018 Volume 10, Issue 2

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Introducing organic   pp111 - 112
Bruce Gibb
As another semester of organic chemistry comes to a close, Bruce Gibb looks back on what he has learned about learning.

News and Views


Solution-phase reaction dynamics: Gaining control   pp113 - 114
Amanda S. Case
Using infrared light to control the outcome of a chemical reaction is problematic in solution because of numerous interactions and non-specific sample heating. Now, condensed-phase results showing the vibrational enhancement of an otherwise thermally driven reaction may reinvigorate discussion of the practical applications of vibrational control.

See also: Article by Stensitzki et al.

Mass spectrometry: Raw protein from the top down   pp114 - 116
Kathrin Breuker
Mass spectrometry is a powerful technique for analysing proteins, yet linking higher-order protein structure to amino acid sequence and post-translational modifications is far from simple. Now, a native top-down method has been developed that can provide information on higher-order protein structure and different proteoforms at the same time.

See also: Article by Li et al.

C–H carbonylation: In situ acyl triflates ace it   pp116 - 117
Yong Ho Lee and Bill Morandi
A simple palladium catalyst has mediated the facile formation of aroyl triflates — an extremely reactive class of electrophiles. These intermediates, generated in situ, enable the Friedel-Crafts acylation of traditionally unreactive arenes, addressing a significant gap in C–H carbonylation methodology.

See also: Article by Garrison Kinney et al.

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Biocatalytic site- and enantioselective oxidative dearomatization of phenols   pp119 - 125
Summer A. Baker Dockrey, April L. Lukowski, Marc R. Becker and Alison R. H. Narayan

Within natural product biosynthetic pathways, nature has evolved highly selective catalysts capable of complexity-generating reactions. Leveraging these tools, a suite of catalysts with complementary site- and stereoselectivity have been applied to the oxidative dearomatization of phenolic compounds, enabling one-pot transformations of phenols into various natural products.
Chemical compounds

Acceleration of a ground-state reaction by selective femtosecond-infrared-laser-pulse excitation   pp126 - 131
Till Stensitzki, Yang Yang, Valeri Kozich, Ashour A. Ahmed, Florian Kössl et al.

A practical realization of selective IR-driven reaction-rate control has been hampered by competing processes leading to sample heating. Now, the acceleration of a bimolecular ground-state reaction in solution using the IR excitation of a vibration connected to the reaction coordinate is demonstrated. The behaviour is monitored and understood using a combination of femtosecond IR-pump IR-probe spectroscopy and theoretical calculations.

See also: News and Views by Case

Artificial muscle-like function from hierarchical supramolecular assembly of photoresponsive molecular motors   pp132 - 138
Jiawen Chen, Franco King-Chi Leung, Marc C. A. Stuart, Takashi Kajitani, Takanori Fukushima et al.

A centimetre-long string formed by the hierarchical self-assembly of a photoresponsive amphiphilic molecular motor — composed of 95 wt% of water — undergoes muscle-like contraction. Under irradiation, rotary motion at the molecular level is amplified through non-covalent interactions to sustain a fast macroscopic mechanical motion of large amplitude.
Chemical compounds

An integrated native mass spectrometry and top-down proteomics method that connects sequence to structure and function of macromolecular complexes   pp139 - 148
Huilin Li, Hong Hanh Nguyen, Rachel R. Ogorzalek Loo, Iain D. G. Campuzano and Joseph A. Loo

An integrated native mass spectrometry and top-down proteomics method using Fourier transform ion cyclotron resonance has been developed for the characterization of macromolecular protein complexes. This approach directly yields primary to quaternary structural information in a single native top-down experiment.

See also: News and Views by Breuker

Theory-driven design of high-valence metal sites for water oxidation confirmed using in situ soft X-ray absorption   pp149 - 154
Xueli Zheng, Bo Zhang, Phil De Luna, Yufeng Liang, Riccardo Comin et al.

Water oxidation is key to the production of chemical fuels from electricity. Now, guided by theory, NiCoFeP oxyhydroxide catalysts have been developed that require an overpotential lower than that required by IrO2. In situ soft X-ray absorption studies of neutral-pH NiCoFeP catalysts indicate formation of Ni4+, which is favourable for water oxidation.

Programmable autonomous synthesis of single-stranded DNA   pp155 - 164
Jocelyn Y. Kishi, Thomas E. Schaus, Nikhil Gopalkrishnan, Feng Xuan and Peng Yin

Primer exchange reaction (PER) cascades have now been used to grow nascent single-stranded DNA with user-specified sequences following prescribed reaction pathways. PER synthesis occurs in a programmable, autonomous, in situ and environmentally responsive fashion, providing a platform for engineering molecular circuits and devices with a wide range of sensing, monitoring, recording, signal processing and actuation capabilities.

Direct α-C–H bond functionalization of unprotected cyclic amines   pp165 - 169
Weijie Chen, Longle Ma, Anirudra Paul and Daniel Seidel

Cyclic amines bearing α-substituents are valuable building blocks for drug discovery and natural product synthesis. Introduction of α-substituents via site-selective replacement of C–H bonds is highly attractive but typically limited to protected amine substrates. Now, an operationally simple hydride-transfer-based approach enables the introduction of α-substituents on unprotected amines.
Chemical compounds

Structure-based inhibitors of tau aggregation   pp170 - 176
P. M. Seidler, D. R. Boyer, J. A. Rodriguez, M. R. Sawaya, D. Cascio et al.

Tau aggregation is associated with Alzheimer's disease and dozens of related dementias. Now atomic structures of the aggregation-prone segment VQIINK in repeat 2 of tau have been reported. Inhibitors designed using these structures block seeding by full-length tau better than inhibitors that target the VQIVYK aggregation segment in repeat 3.

Coherent wavepackets in the Fenna–Matthews–Olson complex are robust to excitonic-structure perturbations caused by mutagenesis   pp177 - 183
Margherita Maiuri, Evgeny E. Ostroumov, Rafael G. Saer, Robert E. Blankenship and Gregory D. Scholes

Spectroscopists and theorists are closing in on an understanding of the origin of oscillatory features in the spectral response of light-harvesting complexes to femtosecond pulsed excitation. Now, the photosynthetic Fenna–Matthews–Olson complex is probed by femtosecond pump–probe spectroscopy and compared with a series of genetically modified mutants with distinct excitonic interactions, allowing electronic and vibrational contributions to coherence to be distinguished.

DNA-imprinted polymer nanoparticles with monodispersity and prescribed DNA-strand patterns   pp184 - 192
Tuan Trinh, Chenyi Liao, Violeta Toader, Maciej Barlóg, Hassan S. Bazzi et al.

DNA–polymer conjugates are attractive materials that combine the programmability of nucleic acid assembly with polymer functionality. Now, through a DNA cube template, monodisperse polymer particles have been imprinted with several DNA strands in pre-designed orientations— each independently set and addressable. The resulting hybrid particles can further assemble into well-defined, non-centrosymmetric structures.

A general approach to intermolecular carbonylation of arene C–H bonds to ketones through catalytic aroyl triflate formation   pp193 - 199
R. Garrison Kinney, Jevgenijs Tjutrins, Gerardo M. Torres, Nina Jiabao Liu, Omkar Kulkarni et al.

Catalytic transformations that incorporate carbonyl functional groups in arene C–H bonds have remained limited, despite being attractive synthetic steps. Now, the intermolecular carbonylative coupling of a broad range of simple arenes into ketones has been developed. The reaction occurs through the palladium-catalysed generation of high-energy aroyl triflate electrophiles.
Chemical compounds
See also: News and Views by Lee & Morandi

Oxidase catalysis via aerobically generated hypervalent iodine intermediates   pp200 - 204
Asim Maity, Sung-Min Hyun and David C. Powers

Oxidation chemistry is critical to introducing molecular complexity during chemical synthesis. Development of sustainable oxidation chemistry demands strategies to harness O2 as a terminal oxidant. Access to hypervalent iodine compounds — a class of broadly useful chemical oxidants — from O2 increases the scope of aerobic oxidation chemistry that can be achieved.
Chemical compounds

Decarboxylative alkylation for site-selective bioconjugation of native proteins via oxidation potentials   pp205 - 211
Steven Bloom, Chun Liu, Dominik K. Kölmel, Jennifer X. Qiao, Yong Zhang et al.

Selectively targeting native amino acids for late-stage protein modification is a significant challenge, but now it has been shown that photoredox catalysis can be used to specifically target protein C-termini toward decarboxylative-alkylation with Michael acceptors. This technology harnesses innate differences in side-chain oxidation potentials to select between the various functional groups typical among proteins in order to form a single modified product.
Chemical compounds

Phosphorylation, oligomerization and self-assembly in water under potential prebiotic conditions   pp212 - 217
Clémentine Gibard, Subhendu Bhowmik, Megha Karki, Eun-Kyong Kim and Ramanarayanan Krishnamurthy

Phosphorylation of (pre)biological molecules in water has been a long-sought goal in prebiotic chemistry. Now, it has been demonstrated that diamidophosphate phosphorylates nucleosides, amino acids and glycerol/fatty acids in aqueous medium, while simultaneously leading to higher-order structures such as oligonucleotides, peptides and liposomes in the same reaction mixture.

Iridium-catalysed arylation of C–H bonds enabled by oxidatively induced reductive elimination   pp218 - 224
Kwangmin Shin, Yoonsu Park, Mu-Hyun Baik and Sukbok Chang

The direct arylation of C–H bonds is an attractive synthetic step, but the reductive elimination of an organometallic catalyst carrying the desired C–H and aryl functionalities has remained challenging. Now, this step has been achieved by first oxidizing the iridium centre of the catalyst, which facilitates the arylation of arene C–H bonds of a range of substrates.
Chemical compounds

Thermally activated delayed photoluminescence from pyrenyl-functionalized CdSe quantum dots   pp225 - 230
Cédric Mongin, Pavel Moroz, Mikhail Zamkov and Felix N. Castellano

The ability to merge the photophysical properties of semiconductor quantum dots with those of well-understood and inexpensive molecular chromophores is important for the development of various emerging photonic and optoelectronic technologies. Now, 1-pyrenecarboxylic acid-functionalized CdSe quantum dots have been shown to undergo thermally activated delayed photoluminescence and display tunable photophysical properties.

A dual role for a polyketide synthase in dynemicin enediyne and anthraquinone biosynthesis   pp231 - 236
Douglas R. Cohen and Craig A. Townsend

The anthraquinone and enediyne halves of the antitumor antibiotic dynemicin A were previously thought to be assembled by two separate polyketide synthases (PKS). Now, a single polyketide synthase has been proposed to be responsible for their production, and a working model for their biosynthesis from a common octaketide intermediate has been suggested.

Labelling and determination of the energy in reactive intermediates in solution enabled by energy-dependent reaction selectivity   pp237 - 241
Hiroaki Kurouchi and Daniel A. Singleton

Short-lived intermediates in solution may react before undergoing thermal equilibration. This phenomenon is used here to achieve the ‘energy labelling’ of an alkoxy radical. The intermediate's excess energy varies broadly depending on how it is formed and can be determined from the observed reaction selectivity.
Chemical compounds

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Corrigendum: Structural snapshots of concerted double E-H bond activation at a transition metal centre   p242
Joseph A. B. Abdalla, Alexa Caise, Christian P. Sindlinger, Remi Tirfoin, Amber L. Thompson et al.



Erratum: Activate lattice oxygen redox reactions in metal oxides to catalyse oxygen evolution   p242
Alexis Grimaud, Oscar Diaz-Morales, Binghong Han, Wesley T. Hong, Yueh-Lin Lee et al.

In Your Element


The germination of germanium   p244
Shawn C. Burdette and Brett F. Thornton
Shawn C. Burdette and Brett F. Thornton explore how germanium developed from a missing element in Mendeleev's periodic table to an enabler for the information age, while retaining a nomenclature oddity.

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