ChemistryOpen

Cover image for Vol. 5 Issue 3

Early View (Online Version of Record published before inclusion in an issue)

Editors: Karen Hindson, Haymo Ross; Deputy Editor: Kate Lawrence

Impact Factor: 3.585

ISI Journal Citation Reports © Ranking: 2015: 42/163 (Chemistry Multidisciplinary)

Online ISSN: 2191-1363

Associated Title(s): Angewandte Chemie International Edition, Chemistry - A European Journal, Chemistry – An Asian Journal

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  1. Full Papers

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      Synthesis of a New Series of Sialylated Homo- and Heterovalent Glycoclusters by using Orthogonal Ligations

      Dr. Gour Chand Daskhan, Carlo Pifferi and Prof. Dr. Olivier Renaudet

      Version of Record online: 22 JUL 2016 | DOI: 10.1002/open.201600062

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      Extending molecular diversity: A straightforward convergent protocol based on orthogonal chemoselective ligations is described to generate heteromultivalency in a controlled manner. Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and thiol-ene coupling (TEC) are first used to functionalize cyclopeptide scaffolds with propargyl and thiol glycosides to generate tetravalent heteroglycoclusters with 2:2 combinations of sugars. In addition, these compounds can be easily (hetero)dimerized by pH-dependent sequential coupling with diethyl squarate to afford various octavalent structures.

  2. Communications

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      Synthesis of Trimeric Organozinc Compounds and their Subsequent Reaction with Oxygen

      Dr. Joe A. Manzi, Dr. Caroline E. Knapp, Prof. Ivan P. Parkin and Prof. Claire J. Carmalt

      Version of Record online: 15 JUL 2016 | DOI: 10.1002/open.201600040

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      Cycle route: A cyclic trimeric organozinc compound of the type [{Zn(Et)(β-diketonate)}3] is described and structurally characterized for the first time. The selective oxidation of species of this type produces [{Zn(β-diketonate)2Zn(Et)OEt}2], allowing a high oxygen content, structural stability, and suitability as precursors to zinc oxide thin films through aerosol-assisted chemical vapor deposition (AACVD).

  3. Full Papers

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      Bio-inspired Dynamic Gradients Regulated by Supramolecular Bindings in Receptor-Embedded Hydrogel Matrices

      Xinglong Luan, Prof. Dr. Yihe Zhang, Dr. Jing Wu, Prof. Dr. Pascal Jonkheijm, Prof. Dr. Guangtao Li, Prof. Dr. Lei Jiang, Prof. Dr. Jurriaan Huskens and Dr. Qi An

      Version of Record online: 30 JUN 2016 | DOI: 10.1002/open.201600030

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      Dynamic gradients: The kinetics of supramolecular bindings is employed in a diffusion process to regulate molecular spatial–temporal distributions. The diffusible guest, 4-aminoazobenzene, quickly and reversibly binds to matrices-bound cyclodextrin during diffusion and generates steeper gradients than regular diffusion. Weakened bindings induced by UV irradiation extend the gradients. A gradient within 4 mm could be preserved for up to 90 h through the coupled “binding–diffusion” process.

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      A Ferrocenyl-Backboned Unsymmetric O,C-Coordinating Ligand and Its Tin Derivatives

      Bastian Janssen, Michael Lutter, Hazem Alnasr, Prof. Dr. Ingo Krossing and Prof. Dr. Klaus Jurkschat

      Version of Record online: 15 JUN 2016 | DOI: 10.1002/open.201600048

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      Put your backbone into it! Changing the Lewis acidity of the tin center on going from SnPh3 via SnIPh2 to SnPh2+ increases the strength of the intra- and intermolecular P=O[RIGHTWARDS ARROW]Sn coordination in the corresponding phosphonyl-substituted ferrocene derivatives to the extent that a ferrocenyl-backboned dinuclear dication, as its salt with the non-coordinating aluminate anion [Al{OC(CF3)3}4], can be isolated.

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      Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

      Prof. Jacek W. Morzycki, Dr. Lucie Rárová, Dr. Jiři Grúz, Tomasz Sawczuk, Urszula Kiełczewska, Dr. Leszek Siergiejczyk and Dr. Agnieszka Wojtkielewicz

      Version of Record online: 15 JUN 2016 | DOI: 10.1002/open.201600027

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      Trying to improve nature: Natural analogues of vitamin A and curcumin exhibit a variety of biological activities. A series of aromatic retinoids and curcuminoids are synthesized and tested in terms of their antiproliferative, antioxidant, and anti-inflammatory activity. The examined compounds exhibit strong anti-inflammatory potency in vitro without affecting cell viability of endothelial cells, as well as antiproliferative activity in the micromolar range.

  4. Reviews

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      “Rules of Engagement” of Protein–Glycoconjugate Interactions: A Molecular View Achievable by using NMR Spectroscopy and Molecular Modeling

      Dr. Roberta Marchetti, Dr. Serge Perez, Dr. Ana Arda, Dr. Anne Imberty, Dr. Jesus Jimenez-Barbero, Prof. Alba Silipo and Prof. Antonio Molinaro

      Version of Record online: 7 JUN 2016 | DOI: 10.1002/open.201600024

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      Rules of engagement: This review focuses on the development and use of modern nuclear magnetic resonance (NMR) techniques, complementing molecular modeling methodologies, able to provide a complete picture of protein–glycoconjugate binding mechanisms related to biomedicine applications against infectious diseases.

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      Synthesis and Alkali-Metal-Ion Complexation of P-Stereogenic Diphosphacrowns

      Prof. Dr. Yasuhiro Morisaki, Ryosuke Kato and Prof. Dr. Yoshiki Chujo

      Version of Record online: 2 JUN 2016 | DOI: 10.1002/open.201600033

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      Crown a new winner: The synthesis of enantiopure aliphatic diphosphacrowns with 12-, 15-, 18-, and 21-membered rings from P-stereogenic secondary bisphosphines is reported. The complexation of alkali metal ions is disclosed, in addition to that of benzo-18-diphosphacrown-6 and benzo-18-crown-6. Diphosphacrowns selectively form a 1:1 complex with smaller alkali metal ions, as compared to the common crown ethers; for example, 18-diphosphacrown-6 prefers Na+ to K+.

  6. Communications

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      Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Dibenzylidene Ketones

      Dan Du, Yu Jiang, Qin Xu, Xiao-Ge Li and Prof. Dr. Min Shi

      Version of Record online: 25 MAY 2016 | DOI: 10.1002/open.201600034

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      Good to be picky: On the basis of asymmetric regioselective [3+2] cycloaddition of 3-isothiocyanato oxindoles with dibenzylidene ketones, the corresponding spirooxindole enols could be obtained in high yields with good-to-excellent diastereo- and enantioselectivities.

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      A Step in Between: [Sn3Bi3]5− and Its Structural Relationship to [Sn3Bi5]3− and [Sn4Bi4]4−

      Ute Friedrich and Prof. Dr. Nikolaus Korber

      Version of Record online: 25 MAY 2016 | DOI: 10.1002/open.201600037

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      Cage fight: The new crown-like [Sn3Bi3]5− anion can be seen as the missing link between the also new [Sn3Bi5]3− anion and the previously reported [Sn4Bi4]4− anion. Both cages are formally derived by capping the crown with either a Bi−Bi or a Sn−Bi dumbbell. The main structural and electronic features of the fragment are conserved, especially the three-center bond of the Sn triangle.

  7. Full Papers

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      Asymmetric Bilayer Muscles: Cooperative Actuation, Dynamic Hysteresis, and Creeping in NaPF6 Aqueous Solutions

      Dr. Masaki Fuchiwaki, Dr. Jose G. Martinez and Prof. Dr. Toribio Fernandez Otero

      Version of Record online: 20 MAY 2016 | DOI: 10.1002/open.201600012

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      Bringing in the muscle: Cooperative dynamic effects (swelling/shrinking) driven by reactions in asymmetric bilayers of two conducting polymers cause a large angular displacement per unit of charge.

  8. Communications

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      Synthesis of β-Hydroxysulfides from Thiophenols and Disulfides with tert-Butyl Hydroperoxide as the Oxidant and Reactant

      Jian-Bo Feng and Prof. Dr. Xiao-Feng Wu

      Version of Record online: 17 MAY 2016 | DOI: 10.1002/open.201600023

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      Quick to react: A procedure for the oxidative synthesis of β-hydroxysulfides is reported, in which thiophenols or diaryl disulfides are reacted with tert-butyl hydroperoxide (TBHP). In the presence of zinc iodide or potassium iodide, with TBHP as the oxidant and pre-reactant, thiophenols and diaryl disulfides react with the methyl group of tBuOH smoothly and selectivity to give the corresponding 2-methyl-1-(arylthio)propan-2-ols as the terminal products in moderate to good yields.

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      Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether

      Dr. John D. Stenger-Smith, Dr. Lawrence Baldwin, Andrew Chafin and Dr. Paul A. Goodman

      Version of Record online: 3 MAY 2016 | DOI: 10.1002/open.201600013

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      Finally! Many asymmetric alkyl tetrahydrofurfuryl ethers are available, and they have a wide range of potential applications. However, the preparation of the symmetric molecule, bis(tetrahydrofurfuryl) ether (BTHFE), has remained elusive, until now. High-purity BTHFE has been prepared and fully characterized for the first time. In addition, a preliminary investigation of BTHFE as a solvent in electrochemical supercapacitors is reported.

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      Hexagonal Lyotropic Liquid Crystal from Simple “Abiotic” Foldamers

      Yu Chen, Zhiqiang Zhao, Dr. Zheng Bian, Dr. Rizhe Jin, Dr. Chuanqing Kang, Dr. Xuepeng Qiu, Dr. Haiquan Guo, Dr. Zhijun Du and Dr. Lianxun Gao

      Version of Record online: 27 APR 2016 | DOI: 10.1002/open.201600007

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      Total recoil: A novel foldamer scaffold, in which p-phenyleneethynylene units are linked by chiral carbon atoms, is reported. In very dilute solutions, these oligomers are random coils. The hexamer and octamers form a hexagonal lyotropic liquid crystal in CH2Cl2 when the concentrations reach the critical values.

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      A Straightforward Electrochemical Approach to Imine- and Amine-bisphenolate Metal Complexes with Facile Control Over Metal Oxidation State

      Michael R. Chapman, Susan E. Henkelis, Prof. Nikil Kapur, Dr. Bao N. Nguyen and Dr. Charlotte E. Willans

      Version of Record online: 15 APR 2016 | DOI: 10.1002/open.201600019

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      Smooth salen! Electrochemical synthesis has provided easy access to 34 complexes of diverse metal–ligand combinations. Facile control over metal oxidation state was possible through slight modification of reaction conditions. Remarkably, selective metallation using a Mn/Ni alloy furnished analytically pure Mn complexes in high yield.

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      Melting Point Distribution Analysis of Globally Approved and Discontinued Drugs: A Research for Improving the Chance of Success of Drug Design and Discovery

      Dr. Fei Mao, Qingya Kong, Wei Ni, Xiang Xu, Dazheng Ling, Zhengyu Lu and Prof. Jian Li

      Version of Record online: 21 MAR 2016 | DOI: 10.1002/open.201600015

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      Mysteries of melting points! Herein, we report the largest melting point (MP) database (experimental value) of globally approved and discontinued drugs. We subsequently extracted six subdatabases from the “approved” database and two from the “discontinued” database and studied the MP distributions and the relationships of molecular weight versus MP, Clog P versus MP distributions. We revealed five noteworthy observations, hoping to provide a theoretical foundation for designing new chemical entities with good drug-like properties.

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