Angewandte Chemie International Edition

Cover image for Vol. 55 Issue 7

Chefredakteur: Peter Gölitz, Stellvertreter: Neville Compton, Haymo Ross

Online ISSN: 1521-3773

Associated Title(s): Angewandte Chemie, Chemistry - A European Journal, Chemistry – An Asian Journal, ChemistryOpen, ChemPlusChem, Zeitschrift für Chemie

Upcoming Hot Papers

Hot Papers are chosen by the Editors for their importance in a rapidly evolving field of high current interest. Many of the "Very Important Papers" (VIPs) would certainly qualify to be included here, but such a duplication is avoided.

Sequence-Defined Polymers

Triazine-Based Sequence-Defined Polymers with Side-Chain Diversity and Backbone–Backbone Interaction Motifs

Dr. Jay W. Grate, Dr. Kai-For Mo and Dr. Michael D. Daily

Triazine-Based Sequence-Defined Polymers with Side-Chain Diversity and Backbone–Backbone Interaction Motifs

The sequence of monomers in macromolecules leads to diverse structures and functions. Nucleophilic aromatic substitution reactions of cyanuric chloride, using a submonomer solid-phase synthesis, have been harnessed to develop a new architecture for sequence-defined polymers with side-chain diversity and noncovalent backbone–backbone interactions.

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Nitrogen Heterocycles

Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives

Simon M. Nicolle, Dr. William Lewis, Prof. Dr. Christopher J. Hayes and Prof. Dr. Christopher J. Moody

Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N−H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives

The metal-catalyzed reaction of diazocarbonyl compounds with β-aminoketone derivatives leads to highly substituted pyrrolidines with excellent diastereoselectivity under mild reaction conditions. The reaction starts as a metallocarbene N−H insertion but is diverted by an intermolecular aldol reaction.

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Nanomedicine

Polymeric Nanoparticles Amenable to Simultaneous Installation of Exterior Targeting and Interior Therapeutic Proteins

Dr. Xi Zhu, Dr. Jun Wu, Wei Shan, Dr. Wei Tao, Dr. Lili Zhao, Dr. Jong-Min Lim, Mathew D'Ortenzio, Prof. Rohit Karnik, Prof. Yuan Huang, Prof. Jinjun Shi and Prof. Omid C. Farokhzad

Polymeric Nanoparticles Amenable to Simultaneous Installation of Exterior Targeting and Interior Therapeutic Proteins

Drug delivery: A novel polymeric nanoparticle platform that is capable of installing protein ligands on the particle surface and simultaneously carrying therapeutic proteins inside was developed by self-assembly. The surface coating with transferrin drastically changed the cellular behavior of the nanoparticles and enhanced the transepithelial transport by transcytosis.

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Enantioselective Catalysis

Catalytic SN2′- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis

Ying Shi and Prof. Amir H. Hoveyda

Catalytic SN2′- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis

Combination catalysis: The first examples of catalytic enantioselective allylic substitution reactions that introduce a CH2−B(pin) unit are described (pin=pinacolato). In combination with various catalytic cross-coupling processes, a range of important organic molecules are now readily accessible.

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Organic Electronics

Synthesis of Nitrogen-Containing Rubicene and Tetrabenzopentacene Derivatives

Dr. Young S. Park, Dr. David J. Dibble, Dr. Juhwan Kim, Robert C. Lopez, Eriberto Vargas and Prof. Alon A. Gorodetsky

Synthesis of Nitrogen-Containing Rubicene and Tetrabenzopentacene Derivatives

Variants of classic polycyclic aromatic hydrocarbons: Nitrogen-containing rubicenes and tetrabenzopentacenes were prepared via a straightforward approach. The reported synthetic method may enable the development of electron transporting organic semiconductors and the eventual construction of larger carbonaceous systems.

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Porphyrins

Directly Diphenylborane-Fused Porphyrins

Keisuke Fujimoto, Juwon Oh, Prof. Dr. Hideki Yorimitsu, Prof. Dr. Dongho Kim and Prof. Dr. Atsuhiro Osuka

Directly Diphenylborane-Fused Porphyrins

A clear expansive π: Diphenylborane-fused porphyrins were synthesized from the corresponding β-(2-trimethylsilylphenyl)-substituted porphyrins. The porphyrin π-system interacts with the vacant p-orbital of the boron. Pyridine adds at the boron center erasing the electronic interaction.

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NMR Spectroscopy

Rapid Determination of Fast Protein Dynamics from NMR Chemical Exchange Saturation Transfer Data

Yina Gu, Dr. Alexandar L. Hansen, Dr. Yu Peng and Prof. Dr. Rafael Brüschweiler

Rapid Determination of Fast Protein Dynamics from NMR Chemical Exchange Saturation Transfer Data

An integrated protocol is reported for the rapid measurement of longitudinal and transverse spin relaxation parameters of proteins using chemical exchange saturation transfer experiments (CEST; see picture). The experiments are suitable for quantitative interpretation by a lean model-free approach (Lean MFA).

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Carbene Transfer Reactions

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Dr. You-Yun Zhou and Prof. Christopher Uyeda

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Nickel interplay: Dinuclear nickel complexes (see scheme) catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source and Zn or Et2Zn as the terminal reductant. Diverse alkenes bearing common functional groups are tolerated under the mildly reducing reaction conditions.

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Single-Molecule Nanocatalysis

Single-Molecule Nanocatalysis Shows In Situ Deactivation of Pt/C Electrocatalysts during the Hydrogen-Oxidation Reaction

Dr. Yuwei Zhang, Tao Chen, Dr. Shaun Alia, Prof. Bryan S. Pivovar and Prof. Dr. Weilin Xu

Single-Molecule Nanocatalysis Shows In Situ Deactivation of Pt/C Electrocatalysts during the Hydrogen-Oxidation Reaction

Catalyst deactivation: By combining single-molecule nanocatalysis with traditional electrochemical methods, the kinetics of the deactivation of a Pt/C electrocatalyst at single-particle level was studied during electrocatalytic hydrogen-oxidation reaction. A correlation between stability and deactivation of the PT/C catalyst was shown.

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C−H Activation

A General Strategy for the Nickel-Catalyzed C−H Alkylation of Anilines

Zhixiong Ruan, Sebastian Lackner and Prof. Dr. Lutz Ackermann

A General Strategy for the Nickel-Catalyzed C−H Alkylation of Anilines

One for all: An inexpensive nickel catalyst enables the C−H alkylation of pyrimidyl anilines with both primary and secondary alkyl halides. The directing group (DG) could be easily removed in a traceless fashion, and the products contain key structural motifs of important anticancer drugs.

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Photoswitching

Giant Amplification of Photoswitching by a Few Photons in Fluorescent Photochromic Organic Nanoparticles

Dr. Jia Su, Prof. Tuyoshi Fukaminato, Dr. Jean-Pierre Placial, Dr. Tsunenobu Onodera, Ryuju Suzuki, Prof. Hidetoshi Oikawa, Arnaud Brosseau, Dr. François Brisset, Dr. Robert Pansu, Prof. Keitaro Nakatani and Dr. Rémi Métivier

Giant Amplification of Photoswitching by a Few Photons in Fluorescent Photochromic Organic Nanoparticles

Amped up: Fluorescent photochromic organic nanoparticles, showing bright red emission, complete ON–OFF contrast with full reversibility, and excellent fatigue resistance, have been prepared. They exhibit a full fluorescence quenching and recovery under light illumination at very low photochromic conversion levels, leading to a “giant amplification of fluorescence photoswitching”.

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Boron OLEDs

Pyridyl Pyrrolide Boron Complexes: The Facile Generation of Thermally Activated Delayed Fluorescence and Preparation of Organic Light-Emitting Diodes

Yi-Jiun Shiu, Yung-Chen Cheng, Wei-Lung Tsai, Prof. Chung-Chih Wu, Chun-Tien Chao, Dr. Chin-Wei Lu, Prof. Yun Chi, Yi-Ting Chen, Dr. Shih-Hung Liu and Prof. Pi-Tai Chou

Pyridyl Pyrrolide Boron Complexes: The Facile Generation of Thermally Activated Delayed Fluorescence and Preparation of Organic Light-Emitting Diodes

Reducing the gap: Using a boron atom as the spiro linker between an electron-deficient pyridyl pyrrolide and an electron-donating phenylcarbazolyl or triphenylamine fragment, boron complexes with a narrow HOMO–LUMO orbital overlap, small singlet–triplet energy gap (down to 38 meV), and strong thermally activated delayed fluorescence (TADF) were prepared. For the first time boron-complex-based OLEDs show a significant TADF contribution.

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Cryopreservation

Combining Biomimetic Block Copolymer Worms with an Ice-Inhibiting Polymer for the Solvent-Free Cryopreservation of Red Blood Cells

Daniel E. Mitchell, Joseph R. Lovett, Prof. Dr. Steven P. Armes and Dr. Matthew I. Gibson

Combining Biomimetic Block Copolymer Worms with an Ice-Inhibiting Polymer for the Solvent-Free Cryopreservation of Red Blood Cells

Antifreeze-free freezing: A wholly synthetic, solvent-free approach for cellular cryopreservation is based on the use of biomimetic block copolymer worms in combination with a well-known ice-recrystallization inhibitor, poly(vinyl alcohol). Upon thawing, red-blood-cell recoveries of up to 70 % were achieved, and free-standing hydrogels were obtained by warming to ambient temperature.

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Post-translational Modifications

Traceless Synthesis of Asymmetrically Modified Bivalent Nucleosomes

Dr. Carolin C. Lechner, Ninad D. Agashe and Dr. Beat Fierz

Traceless Synthesis of Asymmetrically Modified Bivalent Nucleosomes

Make and break: A facile and traceless method to assemble asymmetric post-translationally modified nucleosomes was developed. By using a cleavable peptide tag (the lnc-tag), a library of asymmetric bivalent nucleosomes was generated, which allowed investigation of the intranucleosomal crosstalk between two modifications in the regulation of the histone methyltransferase PRC2.

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HIV

Trimerization of the HIV Transmembrane Domain in Lipid Bilayers Modulates Broadly Neutralizing Antibody Binding

Dr. Timothy M. Reichart, Dr. Michael M. Baksh, Dr. Jin-Kyu Rhee, Dr. Jason D. Fiedler, Prof. Dr. Stephen G. Sligar, Prof. Dr. M. G. Finn, Prof. Dr. Michael B. Zwick and Prof. Dr. Philip E. Dawson

Trimerization of the HIV Transmembrane Domain in Lipid Bilayers Modulates Broadly Neutralizing Antibody Binding

The membrane-proximal external region (MPER) of HIV gp41 is an established target of antibodies that neutralize a broad range of HIV isolates. To evaluate the role of the transmembrane (TM) domain, synthetic MPER-derived peptides were incorporated into lipid nanoparticles and antibody affinity was measured. The studies suggest that neutralizing antibodies can bind the MPER when the TM domain is a three-helix bundle.

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Drug Discovery

Chemoproteomics-Enabled Discovery of a Potent and Selective Inhibitor of the DNA Repair Protein MGMT

Chao Wang, Daniel Abegg, Dominic G. Hoch and Prof. Dr. Alexander Adibekian

Chemoproteomics-Enabled Discovery of a Potent and Selective Inhibitor of the DNA Repair Protein MGMT

Don't fix what is broken: MGMT is an important DNA repair protein, but it also repairs DNA damage caused by chemotherapy in cancer cells. Chloromethyl triazoles (CMTs) are a novel, readily available chemical scaffold for cysteine-reactive covalent inhibitors. Synthesis of a small collection of CMTs leads to the identification of AA-CW236 as the first potent and selective non-pseudosubstrate inhibitor of MGMT.

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O2 Production

Ca2+-Induced Oxidation Generation by FeO42− at pH 910

Dr. Li Ma, Dr. William W. Y. Lam, Dr. Po-Kam Lo, Dr. Kai-Chung Lau and Prof. Tai-Chu Lau

Ca2+-Induced Oxidation Generation by FeO42− at pH 9<b>–</b>10

Calcium can: Although the FeO42− ion is stable in water at pH 9–10, it can be readily activated by Ca2+ ions to generate O2. Similar activating effects are also observed with Mg2+ and Sr2+.

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Total Synthesis

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)-Clavosolide A

Dr. Alba Millán, James R. Smith and Prof. Dr. Varinder K. Aggarwal

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)-Clavosolide A

Growing complexity: A highly efficient and diasteroselective three-component allylboration–Prins reaction serves to construct the highly functionalised THP-ring of (−)-clavosolide A from simple starting materials. An early stage diasteroselective glycosidation and a late stage lithiation–borylation are used to complete the synthesis of this complex natural product in just 13 steps from ethanol in 14 % overall yield.

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Colloidal Crystals

Electroresponsive Structurally Colored Materials: A Combination of Structural and Electrochromic Effects

Tomoya Kuno, Dr. Yoshimasa Matsumura, Dr. Koji Nakabayashi and Prof. Dr. Mahito Atobe

Electroresponsive Structurally Colored Materials: A Combination of Structural and Electrochromic Effects

Coat of many colors: Ordered arrays of polyaniline@poly(methyl methacrylate) core–shell nanoparticles act as electroresponsive structurally colored materials. The colors, which range from greenish-yellow to light-blue, depend on the size of the nanoparticles, and can also be varied by the application of a voltage.

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Glycoproteins

Visualization of Protein-Specific Glycosylation inside Living Cells

Franziska Doll, Annette Buntz, Anne-Katrin Späte, Verena F. Schart, Alexander Timper, Waldemar Schrimpf, Prof. Dr. Christof R. Hauck, Prof. Dr. Andreas Zumbusch and Prof. Dr. Valentin Wittmann

Visualization of Protein-Specific Glycosylation inside Living Cells

Living proof: Protein-specific glycosylation inside living cells was imaged by detecting FRET between an EGFP fused to the protein of interest and a fluorophore ligated to a metabolically incorporated N-acetylglucosamine derivative through an inverse-electron-demand Diels–Alder reaction. FRET can be detected with high contrast even in presence of a large excess of acceptor fluorophores by fluorescence lifetime imaging microscopy (FLIM).

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Gas-Separation Membranes

Hypercrosslinked Additives for Ageless Gas-Separation Membranes

Dr. Cher Hon Lau, Dr. Xavier Mulet, Dr. Kristina Konstas, Dr. Cara M. Doherty, Dr. Marc-Antoine Sani, Prof. Frances Separovic, Dr. Matthew R. Hill and Dr. Colin D. Wood

Hypercrosslinked Additives for Ageless Gas-Separation Membranes

Giving membranes eternal youth: Preventing the collapse of pores in gas-separation membranes vastly improves their lifetime. In fact, the high performance membranes improve with age. The hypercrosslinked polymer additive used for this is cheap to manufacture and has very high processability. This brings the reality of high-performance membranes in the market much closer.

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Sensors

Recognition and Sensing of Creatinine

Dr. Tomàs Guinovart, Daniel Hernández-Alonso, Dr. Louis Adriaenssens, Dr. Pascal Blondeau, Dr. Marta Martínez-Belmonte, Prof. F. Xavier Rius, Dr. Francisco J. Andrade and Prof. Pablo Ballester

Recognition and Sensing of Creatinine

Creatinine quantification: A monophosphonate-bridge calix[4]pyrrole cavitand traps creatinine and the creatininium cation in its deep and polar aromatic cavity. The receptor offers complementary hydrogen-bonding sites to the polar functional groups of the guest. Its use as an ionophore enhances the analytical performance of ion-selective electrodes and enables the determination of creatinine levels in biological samples.

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Graphene Oxide

Graphene Oxide Catalyzed C[BOND]H Bond Activation: The Importance of Oxygen Functional Groups for Biaryl Construction

Dr. Yongjun Gao, Pei Tang, Hu Zhou, Dr. Wei Zhang, Hanjun Yang, Prof. Dr. Ning Yan, Dr. Gang Hu, Prof. Dr. Donghai Mei, Prof. Dr. Jianguo Wang and Prof. Dr. Ding Ma

Graphene Oxide Catalyzed C<img src="http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif" alt="[BOND]" />H Bond Activation: The Importance of Oxygen Functional Groups for Biaryl Construction

A heterogeneous, inexpensive, and environmentally friendly graphene oxide (GO) catalytic system for the C[BOND]H bond arylation of benzene enables the formation of biaryl compounds in the presence of aryl iodides. The oxygen functional groups in these GO sheets and the addition of KOtBu are essential for the observed catalytic activity.

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Nucleic Acid Detection

ATP-Releasing Nucleotides: Linking DNA Synthesis to Luciferase Signaling

Dr. Debin Ji, Michael G. Mohsen, Dr. Emily M. Harcourt and Prof. Dr. Eric T. Kool

ATP-Releasing Nucleotides: Linking DNA Synthesis to Luciferase Signaling

ATP lighting the way: Chimeric dinucleotides were designed to release ATP during polymerase-mediated synthesis of DNA. This ATP can be used to generate a signal with luciferase, thereby allowing the sensitive isothermal detection of both large (phage DNA) and small (miRNA) nucleic acids.

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