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The Chemical Record

Cover image for Vol. 16 Issue 1

February 2016

Volume 16, Issue 1

Pages 1–580

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Personal Account
    5. Record Review
    6. Commentary
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      Cover Picture (page 1)

      Version of Record online: 24 FEB 2016 | DOI: 10.1002/tcr.201590130

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  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Personal Account
    5. Record Review
    6. Commentary
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      Up Close and Personal (pages 2–3)

      Brian P. Johnson

      Version of Record online: 24 FEB 2016 | DOI: 10.1002/tcr.201600006

  3. Personal Account

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Personal Account
    5. Record Review
    6. Commentary
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      Aminoglycoside Antibiotics: New Insights into the Biosynthetic Machinery of Old Drugs (pages 4–18)

      Fumitaka Kudo and Tadashi Eguchi

      Version of Record online: 12 OCT 2015 | DOI: 10.1002/tcr.201500210

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      Step-by-step enzymatic reactions to construct the common biosynthetic intermediates in the biosynthesis of clinically important 2-deoxystreptamine-containing aminoglycoside antibiotics such as neomycin and kanamycin are summarized. Furthermore, recently characterized unique enzymes that are responsible for the diversification of this class of antibiotics are described.

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      Generation of N-Heterocycles via Tandem Reactions of N ′-(2-Alkynylbenzylidene)hydrazides (pages 19–34)

      Guanyinsheng Qiu and Jie Wu

      Version of Record online: 23 OCT 2015 | DOI: 10.1002/tcr.201500219

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      As a powerful synthon, N ′-(2-alkynylbenzylidene)hydrazides have been utilized efficiently for the construction of N-heterocycles. Since N ′-(2-alkynylbenzylidene)hydrazides can easily undergo intramolecular 6-endo cyclization promoted by silver triflate or electrophiles, the resulting isoquinolinium-2-yl amides are amenable to subsequent transformations including [3 + 2] and [3 + 3] cycloadditions and nucleophilic addition.

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      Approaches toward High-Mannose-Type Glycan Libraries (pages 35–46)

      Kohki Fujikawa, Akira Seko, Yoichi Takeda and Yukishige Ito

      Version of Record online: 23 OCT 2015 | DOI: 10.1002/tcr.201500222

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      Systematic chemical synthesis of high-mannose-type glycans overcomes the structural heterogeneity and limited quantity of glycoprotein glycans, and has led to powerful tools for the elucidation of the glycoprotein quality control system in the endoplasmic reticulum. To facilitate a more precise understanding of this system, we proposed a novel methodology named the “top-down-type chemoenzymatic approach”, which provides high-mannose-type glycans in a simplified manner.

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      Radical-Mediated Fluoroalkylations (pages 47–63)

      Eun Jin Cho

      Version of Record online: 26 OCT 2015 | DOI: 10.1002/tcr.201500215

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      Methods have been developed for the installation of trifluoromethyl and difluoroalkyl groups into a variety of organic molecules. The use of eco-friendly resources, such as visible light and non-toxic inorganic electrides, and non-functionalized molecules as substrates, as well as their atom-economical nature, makes these reactions ideal examples of green chemistry.

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      The Chemistry of Heterasumanenes (pages 64–72)

      Masaichi Saito, Shunsuke Furukawa, Junji Kobayashi and Takayuki Kawashima

      Version of Record online: 27 OCT 2015 | DOI: 10.1002/tcr.201500211

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      Our successful synthesis of heterasumanenes, where the benzylic carbon atoms of sumanene are replaced with heteroatoms by stepwise lithiation of the bay regions of the triphenylenes and our original sila-Friedel–Crafts cyclization reactions, is described. The effects of heteroatoms on the structures and optical properties are discussed.

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      Gold-Catalyzed Cyclization Processes: Pivotal Avenues for Organic Synthesis (pages 73–83)

      Amit Kumar, Sukhdev Singh, Sunil K. Sharma, Virinder S. Parmar and Erik V. Van der Eycken

      Version of Record online: 11 NOV 2015 | DOI: 10.1002/tcr.201500230

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      Golden catalysis: Gold-catalyzed approaches have emerged as incredible synthetic opportunities among the scientific community. Due to the trivial reaction conditions and great functional group compatibility, these protocols are synthetically convenient to assemble complex architectures, starting from readily accessible building blocks with high bond forming indices. In this account, we describe the reactivity of various gold catalysts towards intramolecular cyclization processes developed over the years. These protocols give access to a wide scope of polyheterocyclic structures, containing different medium-sized ring skeletons. We envisage that these gold-catalyzed (chemo-/regio-/diastereo-selective) protocols could provide an efficient platform to synthesize biologically important heterocyclic cores and will find their applications in natural product synthesis.

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      Oxygen-Promoted Suzuki–Miyaura Reaction for Efficient Construction of Biaryls (pages 84–97)

      Chun Liu and Xinmin Li

      Version of Record online: 13 NOV 2015 | DOI: 10.1002/tcr.201500218

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      Ligand-free Suzuki–Miyaura reaction systems have recently attracted huge interest. In this account, we will review our recent research on the oxygen-promoted ligand-free Suzuki–Miyaura reaction. The oxygen-promoting effect has been observed in various reaction media, including polyethylene glycol, organic/water mixed solvents and pure water.

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      Design of Organic Transformations at Ambient Conditions: Our Sincere Efforts to the Cause of Green Chemistry Practice (pages 98–123)

      Goutam Brahmachari

      Version of Record online: 17 NOV 2015 | DOI: 10.1002/tcr.201500229

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      The design of synthetic protocols for promising and useful organic reactions at ambient conditions coupled with other green aspects is of current interest in the field of green chemistry practice. The present account summarizes our sincere efforts in designing green synthetic protocols for diverse organic transformations at room temperature and pressure reported during the last five years.

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      Fluorescent Probes Based on Rhodamine Hydrazides and Hydroxamates (pages 124–140)

      Heejeong Moon, Jinyoung Park and Jinsung Tae

      Version of Record online: 17 NOV 2015 | DOI: 10.1002/tcr.201500226

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      Rhodamine hydrazides and hydroxamates have been developed as selective fluorescent probes utilizing either reaction- or chelation-based ring opening of the rhodamine spirolactam. The extra heteroatom (N for hydrazide and O for hydroxamate) serves as a versatile tool for the introduction of multiple binding units and target-specific reaction sites.

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      Our Odyssey with Functionalized Chiral Phosphines: From Optical Resolution to Asymmetric Synthesis to Catalysis (pages 141–158)

      Renta Jonathan Chew and Pak-Hing Leung

      Version of Record online: 18 NOV 2015 | DOI: 10.1002/tcr.201500220

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      Our journey in organophosphorus research over the past 26 years is compiled in this Personal Account. Advances in palladacycle design have engendered a shift in our focus from template-mediated transformations to catalysis for the direct preparation of chiral phosphines that contain a wide variety of functional groups. Novel approaches to access previously inaccessible phosphines and their applications in cancer research are summarized herein.

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      Bipolar Host Materials for Organic Light-Emitting Diodes (pages 159–172)

      Kyoung Soo Yook and Jun Yeob Lee

      Version of Record online: 23 NOV 2015 | DOI: 10.1002/tcr.201500221

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      Bipolar host materials have been widely used as the host materials for organic light-emitting diodes to improve the quantum efficiency. In this work, recent progress in bipolar host materials and their application to OLEDs is reviewed.

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      Accessing the Long-Lived Triplet Excited States in Transition-Metal Complexes: Molecular Design Rationales and Applications (pages 173–188)

      Xiaoneng Cui, Jianzhang Zhao, Zafar Mohmood and Caishun Zhang

      Version of Record online: 30 NOV 2015 | DOI: 10.1002/tcr.201500237

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      Transition-metal complexes with long-lived triplet excited states have a variety of applications in photocatalysis, photovoltaics, photodynamic therapy, and triplet–triplet annihilation upconversion. The development of this area, including the photophysical considerations, molecular design rationales, and applications, is summarized herein.

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      Tailoring Thermodynamics and Kinetics for Hydrogen Storage in Complex Hydrides towards Applications (pages 189–204)

      Yongfeng Liu, Yaxiong Yang, Mingxia Gao and Hongge Pan

      Version of Record online: 7 DEC 2015 | DOI: 10.1002/tcr.201500224

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      Complex hydrides have attracted increasing attention due to their high gravimetric and volumetric hydrogen densities. By changing the material composition and structure, developing feasible preparation methods, doping high-performance catalysts, optimizing multifunctional additives, creating nanostructures and understanding the interaction mechanisms with hydrogen, the operating temperatures for hydrogen storage in metal amides, alanates and borohydrides are remarkably reduced.

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      Nanoporous Carbons: Looking Beyond Their Perception as Adsorbents, Catalyst Supports and Supercapacitors (pages 205–218)

      Teresa J. Bandosz

      Version of Record online: 11 DEC 2015 | DOI: 10.1002/tcr.201500231

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      Nanoporous carbons are built of distorted graphene layers surrounding pores with sizes ranging from a fraction of a nanometer to hundreds of nanometers. This Personal Account provides the background and the history of our current approach to nanoporous carbons, with a focus on exploring the photoactivity of carbons in visible light and their electronic properties. In particular, the applications of nanoporous carbons as sensors, photocatalysts and solar-cell components are discussed.

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      Tuning Optical Properties and Photocatalytic Activities of Carbon-based “Quantum Dots” Through their Surface Groups (pages 219–230)

      Shengliang Hu

      Version of Record online: 12 DEC 2015 | DOI: 10.1111/tcr.201500225

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      Surface group regulation for tuning properties of carbon-based “quantum dots”: The photophysical and photochemical properties of carbon and graphene quantum dots are more dependent on their surface groups than on their size. Different heterogeneous groups play different roles in engineering electronic structure and controlling photogenerated charge behaviors of these quantum dots.

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      Selective Metal-vapor Deposition on Organic Surfaces (pages 231–248)

      Tsuyoshi Tsujioka

      Version of Record online: 12 DEC 2015 | DOI: 10.1002/tcr.201500235

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      Selective metal-vapor deposition on organic surfaces: Selective metal-vapor deposition, which signifies that metal-vapor atoms are deposited onto a hard organic surface but not onto a soft (low glass transition temperature, low Tg) surface, is introduced. A photochromic diarylethene film shows light-controlled selective deposition, but various organic surfaces including polymers can be utilized. A variety of applications, including electrode patterning of organic devices, micro-thin-film fuses, diffraction grating, electrical bistability for memory devices, and metal-vapor integration have been demonstrated.

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      Photodynamic Activity of Fullerenes and Other Molecules Incorporated into Lipid Membranes by Exchange (pages 249–260)

      Atsushi Ikeda

      Version of Record online: 12 DEC 2015 | DOI: 10.1002/tcr.201500249

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      Photodynamic activity of fullerenes and other molecules incorporated into lipid membranes by exchange: Lipid-membrane-incorporated fullerenes prepared by the exchange method have much higher liposomal stability, fullerene water solubility, and photodynamic activity than those prepared by conventional methods.

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      Versatile Oxidation Methods for Organic and Inorganic Substrates Catalyzed by Platinum-Group Metals on Carbons (pages 261–272)

      Yoshinari Sawama, Shota Asai, Yasunari Monguchi and Hironao Sajiki

      Version of Record online: 15 DEC 2015 | DOI: 10.1002/tcr.201500217

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      Various green oxidation techniques catalyzed by heterogeneous platinum-group metals on carbon are summarized. Platinum-group metals on carbon successfully catalyzed the oxidations of hydrogen, alkynes, alcohols and sulfides based on the oxygen oxidation or dehydrogenation pathways.

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      Recent Progress on Graphene-based Electrochemical Biosensors (pages 273–294)

      Yu Zhang, Jingjing Shen, Huihua Li, Linlin Wang, Dashun Cao, Xiaomiao Feng, Yuge Liu, Yanwen Ma and Lianhui Wang

      Version of Record online: 18 DEC 2015 | DOI: 10.1002/tcr.201500236

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      Recent progress on graphene-based electrochemical biosensors, including enzymatic sensors, nonenzymatic sensors, DNA-based sensors, and immunosensors, etc., are recorded and summarized. The accurate electrochemical detection of many biomolecules, such as glucose, hydrogen peroxide, dopamine, ascorbic acid, uric acid, nicotinamide adenine dinucleotide, DNA, RNA, and carcinoembryonic antigen, etc., has been achieved with excellent performance due to the outstanding properties of graphene-based electrode materials.

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      Surface Modification of Graphene Oxides by Plasma Techniques and Their Application for Environmental Pollution Cleanup (pages 295–318)

      Xiangxue Wang, Qiaohui Fan, Zhongshan Chen, Qi Wang, Jiaxing Li, Aatef Hobiny, Ahmed Alsaedi and Xiangke Wang

      Version of Record online: 21 DEC 2015 | DOI: 10.1002/tcr.201500223

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      The surface grafting of graphene oxides with oxygen-containing functional groups using low-temperature plasma techniques is reviewed. The surface-grafted GOs have high sorption ability in the removal of organic and inorganic pollutants in environmental pollution management.

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      Synthesis of N-Containing Heterocyclic Compounds Using Visible-light Photoredox Catalysis (pages 319–334)

      Lei Zhou, Mohammad Lokman Hossain and Tiebo Xiao

      Version of Record online: 11 JAN 2016 | DOI: 10.1002/tcr.201500228

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      Synthesis of N-containing heterocyclic compounds using visible-light photoredox catalysis: Nitrogen heterocycles represent a highly important class of compounds which are widely used in materials science, agrochemistry, and medicinal chemistry. This account summarizes the synthesis of N-heterocycles using visible-light photoredox catalysis published in the last two years, according to the size and type of the formed N-heterocyclic rings. In the context of seminal works of others in this area, a concise summary of the contributions of the authors is also offered.

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      BODIPY Dye, the Most Versatile Fluorophore Ever? (pages 335–348)

      Jorge Bañuelos

      Version of Record online: 11 JAN 2016 | DOI: 10.1002/tcr.201500238

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      BODIPY dye, the most versatile fluorophore ever? The BODIPY chromophore is a versatile platform for post-functionalization which allows fine tuning of its photophysical signatures. Thus, and after a rational molecular design, tailor-made fluorophores can be developed for the target application field, ranging from optoelectronics (such as tunable laser dyes or molecular antennas) to biophotonics (luminescence sensors, switches and probes, or singlet-oxygen photosensitizers).

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      Molecular Epoxidation Reactions Catalyzed by Rhenium, Molybdenum, and Iron Complexes (pages 349–364)

      Jens W. Kück, Robert M. Reich and Fritz E. Kühn

      Version of Record online: 18 JAN 2016 | DOI: 10.1002/tcr.201500233

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      Molecular epoxidation reactions catalyzed by rhenium, molybdenum, and iron complexes: highly active molecular molybdenum and iron catalysts have emerged, challenging the extraordinary role of methyltrioxorhenium in epoxidation catalysis. Results show the promise that relatively cheap and abundant metals, such as molybdenum and iron, hold for the future of epoxidation catalysis.

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      In Vitro Selection Combined with Ribosomal Translation Containing Non-proteinogenic Amino Acids (pages 365–377)

      Tomoshige Fujino and Hiroshi Murakami

      Version of Record online: 18 JAN 2016 | DOI: 10.1002/tcr.201500239

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      In vitro selection of novel inhibitors from the non-proteinogenic peptide library using a TRAP display.

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      Inducing Planar Orientation in Side-Chain Liquid-Crystalline Polymer Systems via Interfacial Control (pages 378–392)

      Shusaku Nagano

      Version of Record online: 18 JAN 2016 | DOI: 10.1002/tcr.201500232

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      New methods and strategies to control molecular orientation for polymer thin films are proposed in this review. Moreover, they demonstrate the effectiveness and impact of the free surface in thin films on molecular orientation. The film surfaces have not been treated as a major subject to control molecular orientation. New methods were demonstrated for controlling the inner structures (molecular orientation) of polymer films from the surface/interface of thin films.

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      Graft Copolymers with Conducting Polymer Backbones: A Versatile Route to Functional Materials (pages 393–418)

      Lisa T. Strover, Jenny Malmström and Jadranka Travas-Sejdic

      Version of Record online: 20 JAN 2016 | DOI: 10.1002/tcr.201500216

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      Graft copolymers with a conducting polymer backbone are a promising class of materials for diverse applications such as organic electronics, stimuli-responsive surfaces, sensors, and biomedical devices. In this Personal Account, we discuss our work in designing functional surfaces based on these, in the context of broader developments in the field.

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      Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si (pages 419–434)

      Hiroto Yoshida

      Version of Record online: 20 JAN 2016 | DOI: 10.1002/tcr.201500227

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      Diborylation, borylstannylation and carboboration of unsaturated C–C bonds under copper catalysis are described. The synthesis of main-group organometallics containing B, Sn or Si through copper-catalyzed installation of a masked boryl, stannyl or silyl moiety is also presented.

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      An Efficient Amide-Aldehyde-Alkene Condensation: Synthesis for the N-Allyl Amides (pages 435–444)

      Zheng-Jun Quan and Xi-Cun Wang

      Version of Record online: 25 JAN 2016 | DOI: 10.1002/tcr.201500212

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      An efficient amide-aldehyde-alkene condensation: Synthesis for the N-Allyl amides: A general protocol for the direct N-allylation of electron-poor N-heterocyclic amides via an amide-aldehyde-alkene condensation reaction catalyzed by Lewis acids is summarized. The substrate scope with respect to N-heterocyclic amides, aldehydes, and styrenes is discussed.

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      Evaporation-induced Self-assembly Process Controlled for Obtaining Highly Ordered Mesoporous Materials with Demanded Morphologies (pages 445–457)

      Tatsuo Kimura

      Version of Record online: 25 JAN 2016 | DOI: 10.1002/tcr.201500262

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      The concept of the “controlled EISA process” has been proposed on the basis of the overall self-assembly process of not only amphiphilic inorganic-organic pairs, but also free inorganic species and/or extra surfactant molecules, which are accommodated in a final mesostructured material, in which all of them can be tiled closely to fabricate a highly ordered mesostructure.

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      Noble Metal-Iron Oxide Hybrid Nanomaterials: Emerging Applications (pages 458–472)

      Ken Cham-Fai Leung and Shouhu Xuan

      Version of Record online: 25 JAN 2016 | DOI: 10.1002/tcr.201500259

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      An overview of current research activities focusing on the synthesis and applications of nanomaterials from noble metal (e.g., Au, Ag, Pd) and iron oxide (Fe3O4) hybrids is given in this account. By utilizing the advantageous properties of both noble metals and iron oxide, a variety of applications, such as theranostics, gene delivery, biosensing, cell sorting, bioseparation, and catalysis, is discussed and highlighted.

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      Tetrel Bonding Interactions (pages 473–487)

      Antonio Bauzá, Tiddo J. Mooibroek and Antonio Frontera

      Version of Record online: 27 JAN 2016 | DOI: 10.1002/tcr.201500256

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      Tetrel bonding interactions: Tetrel (Tr) bonding is first placed into perspective as a σ-hole bonding interaction with atoms of the Tr family. An sp3 R4Tr unit has four σ-holes with which a Lewis base can form a complex. We then highlight some inspiring crystal structures where Tr bonding is obvious, followed by an account of our own work. We hope that this account serves as an initial guide and source of inspiration for others wishing to exploit this vastly underexplored interaction.

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      Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance (pages 488–506)

      Bozhena S. Komarova, Yury E. Tsvetkov and Nikolay E. Nifantiev

      Version of Record online: 20 JAN 2016 | DOI: 10.1002/tcr.201500245

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      Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance: Glycopyranosyl donors bearing remote participating acyl groups are advantageous tools for stereoselective 1,2-cis-glycosylation.

  4. Record Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Personal Account
    5. Record Review
    6. Commentary
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      Pushing the Boundaries of Chemical Protein Synthesis: The Case of Ubiquitin Chains and Polyubiquitinated Peptides and Proteins (pages 509–519)

      Roman Meledin, Sachitanand M. Mali and Ashraf Brik

      Version of Record online: 19 OCT 2015 | DOI: 10.1002/tcr.201500209

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      Chemical protein synthesis enables precise control over the atomic composition and allows the generation of analogues that are otherwise difficult to achieve. In the current review, we describe recent achievements in the synthesis of large and complex proteins, paving the way for a variety of biochemical and biophysical studies.

  5. Commentary

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Personal Account
    5. Record Review
    6. Commentary
    1. You have free access to this content

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