Org. and Biomol. Chem.

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Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

26 February, 2015 - 15:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00099H, Review ArticleBao Hu, Stephen DiMagno
Nitrogen heterocycles are abundant in natural products and pharmaceuticals. An emerging interest among synthetic chemists is to apply vinyl azides as a pivotal three-atom synthon for the construction of structurally...
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Amido-bridged nucleic acids with small hydrophobic residues enhance hepatic tropism of antisense oligonucleotides in vivo

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00242G, PaperTsuyoshi Yamamoto, Aiko Yahara, Reiko Waki, Hidenori Yasuhara, Fumito Wada, Mariko Harada-Shiba, Satoshi Obika
High scalability of a novel bicyclic nucleoside building block, amido-bridged nucleic acid (AmNA), to diversify pharmacokinetic properties of therapeutic antisense oligonucleotides is described.
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Photoinduced formation of stable Ag-nanoparticles from a ternary ligand-DNA-Ag+ complex

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00295H, PaperDaria V. Berdnikova, Heiko Ihmels, Holger Schonherr, Marc Steuber, Daniel Wesner
The irradiation of a ternary complex between an intercalator crown-ether conjugate, double-stranded DNA, and Ag+ ions leads to the formation of stable Ag nanoparticles.
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Editorial: Supramolecular chemistry in water

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2499-2500
DOI: 10.1039/C5OB90026C, EditorialAnthony P. Davis, Stefan Kubik, Antonella Dalla Cort
This themed collection highlights some of the exciting research in supramolecular chemistry in water.
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Amyloid nanospheres from polyglutamine rich peptides: assemblage through an intermolecular salt bridge interaction

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02589J, CommunicationRahul Mishra, Ashwani K. Thakur
Amyloid fiber formation by two polyglutamine peptides through a nucleation polymerization pathway. An intermolecular salt bridge between the positively charged lysine and the negatively charged glutamate induces the formation of nanospherical amyloids through a non-nucleated pathway.
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A mechanistic proposal for the protodeboronation of neat boronic acids: boronic acid mediated reaction in the solid state

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2555-2560
DOI: 10.1039/C4OB02543A, CommunicationGary Noonan, Andrew G. Leach
Boronic acids that undergo protodeboronation as solids are stable in solution: the solid state organizes them for reaction.
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BF3-Et2O mediated skeletal rearrangements of norbornyl appended cyclopentanediols

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2768-2775
DOI: 10.1039/C4OB02423K, PaperChintada Nageswara Rao, Faiz Ahmed Khan
Synthetically useful norbornyl appended cyclopentenones and pinacolone products are reported during the BF3-Et2O mediated skeletal rearrangement of norbornyl appended cyclopentanediols.
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Ylide formal [4 + 1] annulation

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2530-2536
DOI: 10.1039/C4OB02556C, Review ArticleChunyin Zhu, Ya Ding, Long-Wu Ye
Ylide [4 + 1] annulation: beyond small-ring formation.
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Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards [gamma]-lactams and [gamma]-lactones

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2716-2725
DOI: 10.1039/C4OB02615B, PaperKaren Mollet, Lena Decuyper, Saskia Vander Meeren, Nicola Piens, Karel De Winter, Tom Desmet, Matthias D'hooghe
Trans- and cis-2-aryl-3-(2-cyanoethyl)aziridines were transformed into 4-[aryl(alkylamino)methyl]butyrolactones and/or 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones via chemical and enzymatic hydrolysis of the cyano group, followed by ring expansion.
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Computational design of novel peptidomimetic inhibitors of cadherin homophilic interactions

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2570-2573
DOI: 10.1039/C4OB02538E, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Fabio Doro, Cinzia Colombo, Chiara Alberti, Daniela Arosio, Laura Belvisi, Cesare Casagrande, Roberto Fanelli, Leonardo Manzoni, Emilio Parisini, Umberto Piarulli, Elena Luison, Mariangela Figini, Antonella Tomassetti, Monica Civera
Peptidomimetic 3 mimicking the DWVI adhesive sequence of the cadherin EC1 domain inhibits cadherin-mediated adhesion in epithelial ovarian cancer cells.
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Volatiles from nineteen recently genome sequenced actinomycetes

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2673-2683
DOI: 10.1039/C4OB02609H, PaperChristian A. Citron, Lena Barra, Joachim Wink, Jeroen S. Dickschat
The volatiles from nineteen genome sequenced actinobacteria were analysed by GC/MS and the identified terpenes were correlated to genome data.
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Domino [4 + 1]-annulation of [small alpha],[small beta]-unsaturated [small delta]-amino esters with Rh(II)-carbenoids - a new approach towards multi-functionalized N-aryl pyrrolidines

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2640-2651
DOI: 10.1039/C4OB02454K, PaperJ. J. Medvedev, O. S. Galkina, A. A. Klinkova, D. S. Giera, L. Hennig, C. Schneider, V. A. Nikolaev
Catalytic decomposition of diazoesters using Rh(II)- and Cu(II)-complexes in the presence of [small delta]-amino-[small alpha],[small beta]-unsaturated esters produces multi-functionalized pyrrolidines.
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Synthesis of directly fused porphyrin dimers through Fe(OTf)3-mediated oxidative coupling

26 February, 2015 - 15:54

Org. Biomol. Chem., 2015, 13,2566-2569
DOI: 10.1039/C4OB02644F, CommunicationChuan-Mi Feng, Yi-Zhou Zhu, Shao-Chun Zhang, Yun Zang, Jian-Yu Zheng
A practical and general Fe(OTf)3-mediated oxidative coupling method was developed for the synthesis of doubly or triply linked porphyrin dimers.
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Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2786-2792
DOI: 10.1039/C4OB02508C, PaperGanesan Bharathiraja, Mani Sengoden, Masanam Kannan, Tharmalingam Punniyamurthy
Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazines via a copper-catalyzed cascade aza-Michael addition, cyclization and aromatization.
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Alkylidene malonates and [small alpha],[small beta]-unsaturated [small alpha][prime or minute]-hydroxyketones as practical substrates for vinylogous Friedel-Crafts alkylations in water catalysed by scandium(III) triflate/SDS

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2793-2799
DOI: 10.1039/C4OB02487G, PaperJens Oelerich, Gerard Roelfes
Alkylidene malonates and [small alpha],[small beta]-unsaturated [small alpha][prime or minute]-hydroxyketones are excellent substrates for the Sc(OTf)3/SDS catalysed Friedel-Crafts alkylation in water.
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Gas phase chemistry of N-benzylbenzamides with silver(I) cations: characterization of benzylsilver cation

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2561-2565
DOI: 10.1039/C4OB02355B, CommunicationHezhi Sun, Zhe Jin, Hong Quan, Cuirong Sun, Yuanjiang Pan
Benzylsilver cations are synthesized in the gas phase from the collisional dissociation of argentinated N-benzylbenzamides, when the carbonyl oxygen nucleophilically attacks an [small alpha]-hydrogen.
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Templating carbohydrate-functionalised polymer-scaffolded dynamic combinatorial libraries with lectins

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2756-2761
DOI: 10.1039/C4OB02587C, PaperClare S. Mahon, Martin A. Fascione, Chadamas Sakonsinsiri, Tom E. McAllister, W. Bruce Turnbull, David A. Fulton
The templation of carbohydrate-functionalised Polymer-Scaffolded Dynamic Combinatorial Libraries affords polymers possessing significantly enhanced affinities for the template, with enhancements in free energy of binding in the range of 5.2-8.8 kJ mol-1 observed.
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Synthesis of a [small beta]-CCT-lanthanide conjugate for binding the dopamine transporter

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2537-2540
DOI: 10.1039/C4OB02165G, CommunicationGregory R. Naumiec, Grace Lincourt, Jeremy P. Clever, Michael A. McGregor, Abraham Kovoor, Brenton DeBoef
The development of a [small beta]-CCT-lanthanide conjugate that binds the dopamine transporter (DAT) with high affinity (Kd = 303 nM) is described. This molecular probe could be used for in vivo or in vitro studies of the DAT via MRI, PET or SPECT.
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Cyclopropanation using flow-generated diazo compounds

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2550-2554
DOI: 10.1039/C5OB00019J, CommunicationNuria M. Roda, Duc N. Tran, Claudio Battilocchio, Ricardo Labes, Richard J. Ingham, Joel M. Hawkins, Steven V. Ley
A practical and mild protocol for the cyclopropanation of unstabilised diazo compounds is reported.
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TEMPO-mediated homocoupling of aryl Grignard reagents: mechanistic studies

24 February, 2015 - 15:17

Org. Biomol. Chem., 2015, 13,2762-2767
DOI: 10.1039/C4OB02689F, PaperSandip Murarka, Juri Mobus, Gerhard Erker, Christian Muck-Lichtenfeld, Armido Studer
The mechanism of TEMPO mediated oxidative homo-coupling of aryl Grignard reagents to biphenyls is investigated in detail by experimental and computational studies.
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