Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• Serge Perez Daniele de Sanctis Department of Molecular Pharmacochemistry, CNRS-University Grenoble Alpes, France ESRF – The European Synchrotron, Grenoble, France 10.3762/bjoc.13.114 Abstract Synchrotron radiation is the most versatile way to explore biological materials in different states

• : monocrystalline, polycrystalline, solution, colloids and multiscale architectures. Steady improvements in instrumentation have made synchrotrons the most flexible intense X-ray source. The wide range of applications of synchrotron radiation is commensurate with the structural diversity and complexity of the

• hydrolases; glycosyl transferases; kinetic crystallography; lectins; polysaccharides; powder diffraction; small-angle X-ray scattering; starch; synchrotron radiation; transporters; X-ray crystallography; Introduction Over the last decade, glycoscience has greatly benefited from the development of structural

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

• Simon Drescher,
• Vasil M. Garamus,
• Christopher J. Garvey,
• Annette Meister and
• Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

• ) SAXS experiments were performed at the P12 BioSAXS beamline of the European Molecular Biology Laboratory (EMBL) at the storage ring PETRA III of the Deutsche Elektronen Synchrotron (DESY, Hamburg, Germany) using a Pilatus 2M detector (1475 × 1679 pixels; Dectris, Switzerland) and synchrotron radiation

• , UK) with accuracy ± 0.1 °C. Twenty consecutive frames (each 0.05 s) comprising the measurement of the solvent (phosphate buffer pH 7.4) and sample were performed. In order to verify that no artefacts as a result of radiation damage occurred, all scattering curves of a recorded dataset were compared

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• cool at a slower rate due to natural convection and to some extent radiation. However, an additional set-up (for cooling the induction coil) is required for this which will add cost. Moreover, air needs to be very clean and possibly moisture free as it can corrode the induction coil. With this complex

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• diseases, inflammatory processes, arthritis, and skin damage caused by exposure to UV radiation [1][2][3]. However, all these properties belong to organoselenides due to their ability to engage in enzymatic processes [4][5] and alkynyl selenides have demonstrated only limited biological properties [6][7

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• a Siemens P4 diffractometer using Cu Kα (λ = 1.54178 Å) radiation for 1 and on a Bruker SMART APEX II diffractometer equipped with APEX II CCD detector using Mo Kα (λ = 0.71073 Å) radiation for 2. The structures were solved by direct methods with the SIR97 program [11] and refined by full-matrix

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• . The X-ray source was Al Kα radiation (1486.6 eV) monochromatized radiation with a pass energy of 20 eV. The emissions of photoelectrons from the sample were analyzed at a take-off angle of 90° under UHV conditions. After collection, the binding energies (BE) were calibrated against the Au4f7/2 BE at

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• species, especially if they are slightly soluble into an aqueous environment, have been proposed to prevent classes of unproductive reactions [7][8]. (iv) Stabilizers. Many useful pre-biological polymers are subject to destruction by environmental forces, such as ultraviolet radiation and radioactivity

NMR reaction monitoring in flow synthesis

• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

• systems for the rapid analysis and optimization of reaction parameters and conditions. The use of this technique in mechanistic studies is also discussed. Review Commercial flow probes NMR spectroscopy is based on the absorption of radiofrequency radiation to produce absorption on the nuclear spin level

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• -ray crystallography were performed on a Bruker Smart Apex CCD area detector diffractometer using graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). Details of the X-ray structure determinations and refinements are provided in Table 5. According to the synthetic procedures in the literature, the

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

• Vinicius R. Campos,
• Ana T. P. C. Gomes,
• Anna C. Cunha,
• Maria da Graça P. M. S. Neves,
• Vitor F. Ferreira and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

• ) irradiation (Table 1, entries 7, 8 and 9). The reactions were carried out under 200 W for 5 minutes at 120 °C. The results obtained show that, under MW radiation, β-alkenylporphyrin derivatives 3a–c were obtained in reasonable yields (between 59 and 69%) and it was possible to recover ca. 20% of porphyrin 1

• %, 1.32 µmol, 1.5 mg), Cs2CO3 (3 equiv, 79.2 µmol, 27.9 mg) and Et4NBr (20 mol %, 5.28 µmol, 1.10 mg). The obtained mixtures were dissolved in toluene (1 mL) and DMF (0.5 mL). The reactions were irradiated under MW radiation under 200 W for 5 minutes at 120 °C. After cooling, the reactions were quenched

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• radiation. The data were collected in the 2θ range 2.3–40° with a step size of 0.02° and a counting time of 0.4 s per step, a primary slit module of 0.6 mm, air scatter screen module 1 mm and secondary slit module 8 mm. Schematic thermodynamic description of the CP process and time constants. The I-S model

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• . Experimental Hexakisadduct C3 [55] and malonate 1 [59] were synthesized according to literature procedures. X-ray crystallography: Bruker D8 Quest diffractometer with Photon 100 CMOS APS detector and Montel multilayer optics monochromated Cu Kα radiation. PXRD diffraction: Bruker D8 Discovery with 1D-Lynxeye

• detector using Cu Kα radiation (unsplit Kα1 + Kα2 doublet, mean wavelength λ = 154.19pm), reflection and transmission geometry. Hexakisadduct 2: C60 (565 mg, 785 µmol, 1 equiv), malonate 1 (3.10 g, 7.84 mmol, 10 equiv) and CBr4 (26.0 g, 78.4 mmol, 100 equiv) were dissolved in dry toluene (500 mL). DBU

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

• Salvatore V. Giofrè,
• Santa Cirmi,
• Raffaella Mancuso,
• Francesco Nicolò,
• Giuseppe Lanza,
• Laura Legnani,
• Agata Campisi,
• Maria A. Chiacchio,
• Michele Navarra,
• Bartolo Gabriele and
• Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

• silica gel 0.040–0.063 mm. X-ray crystal structure determination of compound 6a was performed at room temperature on a suitable single crystal, obtained by recrystallization from ether/dichloromethane 2:1, by a Bruker AXS K Apex II CCD diffractometer with Mo Kα radiation (λ = 0.71073 Å). The structure

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

• Ming Liu,
• Jan C. Namyslo,
• Martin Nieger,
• Mika Polamo and
• Andreas Schmidt

Beilstein J. Org. Chem. 2016, 12, 2673–2681, doi:10.3762/bjoc.12.264

• mass spectrometer with electrospray ionisation. The single-crystal X-ray diffraction studies were carried out on a Bruker D8 Venture diffractometer with Photon100 detector at 123(2) K using Cu Kα (8) and Mo Kα radiation (9, 11, 12) (λ = 1.54178 Å and 0.71073 Å). Dual space methods (8, SHELXT) [53] and

Effects of solvent additive on “s-shaped” curves in solution-processed small molecule solar cells

• John A. Love,
• Shu-Hua Chou,
• Ye Huang,
• Guilllermo C. Bazan and
• Thuc-Quyen Nguyen

Beilstein J. Org. Chem. 2016, 12, 2543–2555, doi:10.3762/bjoc.12.249

• (Award No. N000141410076) for support of this work. T.-Q.N. thanks the Camille Dreyfus Teacher Scholar Award. The authors acknowledge the support of Stanford Synchrotron Radiation Light source (SSRL), which is supported by the U.S. Department of Energy.

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• developed by visualization under UV light (λ = 254 nm). Diffraction data were collected with a Bruker-Nonius Apex-II-diffractometer using graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). The diffraction measurements were performed at −150 °C. The unit cell dimensions were recorded and refined using

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• CDCl3) and coupling constants (J) are given in Hz. ECD spectra were measured on a Chirascan CD spectrometer (Applied Photophysics, London, UK). Single-crystal data were collected on an Agilent Gemini Ultra diffractometer (CuKα radiation). Silica gel (200–300 mesh, Qingdao Marine Chemical Factory) and

• diffraction data were collected at 123 K on an Agilent Gemini Ultra diffractometer with CuKα radiation (λ = 1.54178 Å). The structures were solved by direct methods (SHELXS-97) and refined using full-matrix least-squares difference Fourier techniques. Hydrogen atoms bonded to carbons were placed on the

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• II diffractometer using Cu Kα (λ = 1.54178 Å) radiation monochromated using laterally graded multilayer (Goebel) mirror focusing optics. A single crystal was mounted on a Mitegen loop and cooled to 100 K for data collection. Unit cell parameters were measured and data were collected using the Rigaku

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

• David R. Chisholm,
• Garr-Layy Zhou,
• Ehmke Pohl,
• Roy Valentine and
• Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

• diffractometer (13,14, 15b, 29 and 30) and an Xcalibur Sapphire3 diffractomer (19), using Mo Kα radiation. Crystals were cooled using Cryostream (Oxford Cryosystems) open-flow N2 cryostats. The structures were solved within Olex2 by direct methods and refined by full-matrix least squares against F2 of all data

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• then the resulting pH (pHf) was measured. The difference between the initial and final pH values (ΔpH) was plotted against the initial pH. The PZC was represented by the point ΔpH = 0 [32]. X-ray diffraction analysis (XRD) was performed on a Bruker D8 Advance diffractometer using Cu Kα radiation with a

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

• Josef Schachtner,
• Patrick Bayer and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

• phase, a gas phase, and an electromagnetic radiation field, where an effective interaction of three quasi mobile phases of different physical states is required for high selectivities and conversion rates. Such scenarios are highly relevant for photochemical reactions with reactive gases (e.g., air, O2

Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands

• Dirk Meyer and
• Thomas Strassner

Beilstein J. Org. Chem. 2016, 12, 1557–1565, doi:10.3762/bjoc.12.150

• system (Kappa-CCD; Nonius) at the window of a sealed X-ray tube (Nonius, FR590) and graphite monochromated Mo Kα radiation (λ = 0.72073 Å). The reflections were integrated. Raw data were corrected for Lorentz and polarization and, arising from the scaling procedure, for latent decay. An absorption

Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate

• Sean P. Bew,
• Glyn D. Hiatt-Gipson,
• Graham P. Mills and
• Claire E. Reeves

Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103

• protect them against ’attack’ from bacteria, fungi and parasites. Isoprene also helps to protect against abiotic ’stress’ induced by excessive fluctuations in temperature, by drought, exposure to radiation as well as by contact with herbicides and insecticides [7]. Isoprene reacts readily with O3, HO• and

• and NOX concentrations. The oxidation products derived from monoterpenes have been demonstrated to be important in generating atmospheric based secondary organic aerosols (SOA’s) that have a significant impact on global radiation [54]. Exploiting our methodology further its diversity and application

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• desired product X-ray diffraction analysis Analogously as described in [27], single-crystal X-ray diffraction data were collected at 298(2) K on a Siemens Smart/CCD area-detector or Oxford Diffraction Gemini A Ultra diffractometer with a Mo Kα radiation (λ = 0.71073 Å) by using an ω-2θ scan mode. Unit

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• Pa·s at 298.2 K, respectively, and upon ultraviolet radiation these values decrease ten-fold and increase two-fold reversibly, respectively (Figure 15). This reflects the lesser ability of the 3α-CD substituent to complex either the trans- or cis-azobenzene substituent by comparison with the 6α-CD

• reversibly photo-isomerized from the trans to cis configurations and vice-versa by ultra-violet and visible radiation, respectively, and that the corresponding solution to hydrogel transition temperatures are 299.7 K and 309.7 K for 10 g L−1 azo-HMPC in aqueous 0.5 M NaCl [94]. This is attributed to the

• interesting aspect is that because the α-bromonaphthalene substituents occupy the hydrophobic β-CD annuli in the hydrogel, UV radiation induces room temperature phosphorescence which, in combination with the self-healing properties of the hydrogel, may lead to some interesting applications. The change of