Tuesday, November 22, 2016

Nature Chemistry Contents December 2016 Volume 8 Number 12 pp 1085 - 1168

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TABLE OF CONTENTS

December 2016 Volume 8, Issue 12

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Perspective
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In Your Element
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News and Views

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Macrocyclic peptides: Tying up loose ends   pp1085 - 1086
Fumito Saito and Jeffrey W. Bode
doi:10.1038/nchem.2683
Despite their potential as drugs, peptides are generally not cell permeable, which limits their practical applications in medicine. Now, linear peptides have been cyclized by using a heteroaromatic linker. This cyclization both improves passive membrane permeability and stabilizes a biologically relevant secondary structure.

See also: Article by Frost et al.

C-H activation: Good things come in threes   pp1086 - 1088
Marco Simonetti and Igor Larrosa
doi:10.1038/nchem.2679
Three different methods that use a single ruthenium catalyst to enable the facile formation of meta- and para-substituted alkenylarenes have now been developed. The reactions proceed through a tandem alkenylation/decarboxylation process and provide several advantages over alternative approaches.

See also: Article by Zhang et al.

Antibody-drug conjugates: The missing link   pp1088 - 1090
Tiago Rodrigues and Gonçalo J. L. Bernardes
doi:10.1038/nchem.2685
The targeted release of bioactive molecules to diseased tissues has the potential to improve therapeutic efficacy, but not all drugs contain a free functional group that can be easily attached to an antibody. Now, a linker technology has been developed to enable the traceless release of tertiary and heteroaryl amine-containing drugs.

See also: Article by Staben et al.

2016 Nobel Prize in Chemistry: Molecular machines   p1090
Victoria Richards
doi:10.1038/nchem.2687

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Perspective

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Oriented electric fields as future smart reagents in chemistry   pp1091 - 1098
Sason Shaik, Debasish Mandal and Rajeev Ramanan
doi:10.1038/nchem.2651



No longer a theoretical dream, this perspective describes effects of oriented external electric fields on rates and selectivity patterns of nonpolar reactions. Discussions of the Diels-Alder reaction, C-H and C=C bond activations, etc., underscore the potential usage of oriented electric fields as future smart catalysts, inhibitors and reagents in chemistry.

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Articles

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Mechanically controlled quantum interference in individual π-stacked dimers   pp1099 - 1104
Riccardo Frisenda, Vera A. E. C. Janssen, Ferdinand C. Grozema, Herre S. J. van der Zant and Nicolas Renaud
doi:10.1038/nchem.2588



Single-molecule junctions provide a unique platform to understand how molecular structure affects electronic transport. Now it has been shown that electronic transport through a π-stacked dimer can be precisely controlled when pulling it apart. This behaviour is caused by quantum interference effects that are turned ON or OFF depending on dimer conformation.

Oxadiazole grafts in peptide macrocycles   pp1105 - 1111
John R. Frost, Conor C. G. Scully and Andrei K. Yudin
doi:10.1038/nchem.2636



Controlling macrocycle conformation represents a powerful tool for the construction of new bioactive molecules. Now, peptide-based macrocycles bearing a 1,3,4-oxadiazole moiety grafted into their backbone have been synthesized via a new cyclization approach. The resulting cyclic products exhibit conformationally rigid turn structures (stabilized through intramolecular hydrogen bonding) that can display passive membrane permeability.
Chemical compounds
See also: News and Views by Saito & Bode

Targeted drug delivery through the traceless release of tertiary and heteroaryl amines from antibody–drug conjugates   pp1112 - 1119
Leanna R. Staben, Stefan G. Koenig, Sophie M. Lehar, Richard Vandlen, Donglu Zhang et al.
doi:10.1038/nchem.2635



Many drugs contain tertiary and heteroaryl amines; however, these functional groups are difficult to reversibly crosslink to a carrier protein. Now, a method for conjugating anticancer and antibiotic drugs to antibodies via a quaternary ammonium salt has been developed. Cleavage of the linker results in the traceless release of the free drug and subsequent therapeutic activity.

See also: News and Views by Rodrigues & Bernardes

Enabling singlet fission by controlling intramolecular charge transfer in π-stacked covalent terrylenediimide dimers   pp1120 - 1125
Eric A. Margulies, Claire E. Miller, Yilei Wu, Lin Ma, George C. Schatz et al.
doi:10.1038/nchem.2589



Singlet fission in assemblies of molecular chromophores offers a promising route to improving solar cell efficiencies, but its mechanism is not fully understood. Now, a series of covalently bound π-stacked terrylenediimide dimers have been studied to elucidate the role of interchromophore charge-transfer states in the mechanism of singlet fission.
Chemical compounds

New ligands for nickel catalysis from diverse pharmaceutical heterocycle libraries   pp1126 - 1130
Eric C. Hansen, Dylan J. Pedro, Alexander C. Wotal, Nicholas J. Gower, Jade D. Nelson et al.
doi:10.1038/nchem.2587



Pharmaceutical compound libraries are an essential part of drug discovery and the screening of libraries for new drug leads is routine. It has now been shown that these heterocycle-rich, diverse libraries can also be used for ligand discovery. The discovery and application of several new ligands to nickel-catalysed cross-electrophile coupling is demonstrated.
Chemical compounds

Benzazetidine synthesis via palladium-catalysed intramolecular C−H amination   pp1131 - 1136
Gang He, Gang Lu, Zhengwei Guo, Peng Liu and Gong Chen
doi:10.1038/nchem.2585



Hampered by a lack of practical syntheses, benzazetidines are one of the few rarely explored compounds in N-heterocyclic chemical space. An efficient synthesis of various benzazetidines by Pd-catalysed intramolecular C−H amination of N-benzyl picolinamides is now reported. Reagent-controlled reductive elimination of a Pd intermediate is a key aspect of this particular method.
Chemical compounds

Direct observation of subpicosecond vibrational dynamics in photoexcited myoglobin   pp1137 - 1143
C. Ferrante, E. Pontecorvo, G. Cerullo, M. H. Vos and T. Scopigno
doi:10.1038/nchem.2569



Difficulties in experimentally achieving simultaneous structural sensitivity and time resolution have hindered the real-time mapping of the vibrational energy relaxation pathways in biomacromolecules. Now, using ultrashort light pulses to locally deposit excess energy in a protein-bound haem, the temporal evolution of the subsequent energy flow has been monitored, unravelling vibrational couplings that lead to mode-specific temperature changes.

A decarboxylative approach for regioselective hydroarylation of alkynes   pp1144 - 1151
Jing Zhang, Ruja Shrestha, John F. Hartwig and Pinjing Zhao
doi:10.1038/nchem.2602



Achieving high regioselectivity in hydroarylation of alkynes has been a long-standing challenge. Now, a ruthenium-catalysed decarboxylative alkyne hydroarylation with broad substrate scope, high chemo- and stereoselectivity, as well as controlled and versatile regiochemistry, is described.

See also: News and Views by Simonetti & Larrosa

Mass spectrometry captures off-target drug binding and provides mechanistic insights into the human metalloprotease ZMPSTE24   pp1152 - 1158
Shahid Mehmood, Julien Marcoux, Joseph Gault, Andrew Quigley, Susan Michaelis et al.
doi:10.1038/nchem.2591



Off-target drug binding of anti-HIV protease inhibitors to a zinc metalloprotease has been suspected for some time. Now, mass spectrometry of human zinc metalloprotease ZMPSTE24 in the presence of four inhibitors has provided molecular evidence for this off-target binding. These results also enabled an investigation of the effects of the inhibitors on the processing of farnesylated prelamin A peptides.

The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes   pp1159 - 1166
Haoquan Li, Kaiwu Dong, Haijun Jiao, Helfried Neumann, Ralf Jackstell et al.
doi:10.1038/nchem.2586



The selective formation of Markovnikov products in carbonylation reactions is a challenging problem, especially from unactivated substrates. Now, a highly Markovnikov-selective alkoxycarbonylation reaction is described using a catalyst system based on palladium and the cataCXium ligand POMeCy(Ph). The resulting branched carboxylates are important structural components in many flavour and fragrance products.
Chemical compounds

In Your Element

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Einsteinium declassified   p1168
Joanne Redfern
doi:10.1038/nchem.2676
Discovered during secret testing by the United States, Joanne Redfern tells us about element 99 and why its namesake cautioned against the very technology that led to its creation.

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