Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Acid-promoted direct electrophilic trifluoromethylthiolation of phenols

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,3103-3115
DOI: 10.1039/C4OB02633K, PaperMarjan Jereb, Kaja Gosak
A highly selective and effective, acid-promoted, electrophilic trifluoromethylthiolation of phenols is described.
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Reversal of H-bonding direction by N-sulfonation in a synthetic reverse-turn peptide motif

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,3064-3069
DOI: 10.1039/C4OB02438A, PaperKuruppanthara N. Vijayadas, Amol S. Kotmale, Shridhar H. Thorat, Rajesh G. Gonnade, Roshna V. Nair, Pattuparambil R. Rajamohanan, Gangadhar J. Sanjayan
This manuscript depicts an intriguing example of H-bonding reversal upon introduction of a sulfonamide linkage at the N-terminus of a synthetic reverse-turn peptide.
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Hybridization of an A[small beta]-specific antibody fragment with aminopyrazole-based [small beta]-sheet ligands displays striking enhancement of target affinity

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2974-2979
DOI: 10.1039/C4OB02411G, PaperMarco Hellmert, Andreas Muller-Schiffmann, Max Sena Peters, Carsten Korth, Thomas Schrader
A His-tagged antibody is combined with an NTA-[small beta]-sheet breaker and displays a striking increase in A[small beta] affinity.
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Cyclopenta[b]naphthalene cyanoacrylate dyes: synthesis and evaluation as fluorescent molecular rotors

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2965-2973
DOI: 10.1039/C4OB02563F, PaperLaura S. Kocsis, Kristyna M. Elbel, Billie A. Hardigree, Kay M. Brummond, Mark A. Haidekker, Emmanuel A. Theodorakis
The application of an intramolecular dehydrogenative dehydro-Diels-Alder (IDDDA) reaction to the construction of fluorescent molecular rotors (D-[small pi]-A motif) containing a cyclopenta[b]naphthalene ring system is described.
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Solvent- and phase-controlled photochirogenesis. Enantiodifferentiating photoisomerization of (Z)-cyclooctene sensitized by cyclic nigerosylnigerose-based nanosponges crosslinked by pyromellitate

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2905-2912
DOI: 10.1039/C4OB02390K, PaperXueqin Wei, Wenting Liang, Wanhua Wu, Cheng Yang, Francesco Trotta, Fabrizio Caldera, Andrea Mele, Tomoyuki Nishimoto, Yoshihisa Inoue
The enantioselectivity of the (E)-cyclooctene produced critically depended on the solvent and also on the phase evolved, maximizing at the flowing/rigid gel border.
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Cucurbiturils as supramolecular inhibitors of DNA restriction by type II endonucleases

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2866-2869
DOI: 10.1039/C4OB02122C, CommunicationCatia Parente Carvalho, Amir Norouzy, Vera Ribeiro, Werner M. Nau, Uwe Pischel
Cucurbiturils inactivate the restriction reaction of type II endonucleases via supramolecular interactions. This was monitored for different enzyme-DNA combinations in the absence and presence of organic macrocycles. The process can be re-activated by competitive displacement on addition of polyamines.
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Reaction of [small beta]-enaminones and acetylene dicarboxylates: synthesis of substituted 1,2-dihydropyridinones

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,3011-3023
DOI: 10.1039/C4OB01578A, PaperVemu Nagaraju, Dalovai Purnachander, N. S. V. M. Rao Mangina, Surisetti Suresh, Balasubramanian Sridhar, Galla V. Karunakar
Synthesis of dihydropyridinones was achieved by reaction of [small beta]-enaminones with acetylene dicarboxylates without using transition metal/catalyst.
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Fractional transfer of a free unpaired electron to overcome energy barriers in the formation of Fe4+ from Fe3+ during the core contraction of macrocycles: implication for heme distortion

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2939-2946
DOI: 10.1039/C4OB02429J, PaperQiuhua Liu, Xiaochun Zhou, Haomin Liu, Xi Zhang, Zaichun Zhou
The free unpaired electron in Fe3+ ions cannot be directly removed, and needs a transfer pathway with at least four steps to overcome the high energy barriers to form Fe4+ ions.
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A [gamma]-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2980-2985
DOI: 10.1039/C4OB02464H, PaperSergey Volkov, Lukas Kumprecht, Milos Budesinsky, Martin Lepsik, Michal Dusek, Tomas Kraus
Oxidative dimerization of 6I,6V-disulfanyl-[gamma]-cyclodextrin yields a duplex tubular structure with internal volume of [similar]740 A3 allowing formation of very stable inclusion complexes with medium to large organic molecules in water (Ka [similar] 108 M-1).
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A configurational and conformational study of (-)-Oseltamivir using a multi-chiroptical approach

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2999-3010
DOI: 10.1039/C4OB02369B, PaperMarcin Gorecki
Four chiroptical methods, i.e. electronic circular dichroism (ECD), optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and Raman optical activity (ROA) were employed to discover a set of the most probable conformations of (-)-Oseltamivir in solution.
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Solid-state circularly polarised luminescence of atropisomeric fluorophores embedded in achiral myo-inositol-containing polyurethanes

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2913-2917
DOI: 10.1039/C4OB02553A, PaperTomoyuki Amako, Kazuki Nakabayashi, Atsushi Sudo, Michiya Fujiki, Yoshitane Imai
Two chiral binaphthyl fluorophores in two myo-inositol based polyurethane matrices with high grass transition temperatures emitted circularly polarised luminescence with a high circular anisotropy factor.
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Luminescent organogels based on triphenylamine functionalized [small beta]-diketones and their difluoroboron complexes

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2986-2998
DOI: 10.1039/C4OB02612H, PaperChong Qian, Mingyang Liu, Guanghui Hong, Pengchong Xue, Peng Gong, Ran Lu
New organogelators based on triphenylamine functionalized [small beta]-diketones and their difluoroboron complexes were synthesized.
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NBD-based fluorescent chemosensor for the selective quantification of copper and sulfide in an aqueous solution and living cells

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2918-2926
DOI: 10.1039/C4OB02178A, PaperQingtao Meng, Yu Shi, Cuiping Wang, Hongmin Jia, Xue Gao, Run Zhang, Yongfei Wang, Zhiqiang Zhang
A fluorescent chemosensor (NL) has been developed for the selective quantification of copper and sulfide in aqueous solutions and living cells.
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Supramolecular control of transition metal complexes in water by a hydrophobic cavity: a bio-inspired strategy

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2849-2865
DOI: 10.1039/C4OB02511C, Review ArticleOlivia Bistri, Olivia Reinaud
Different strategies for obtaining water-soluble cavity-appended metal complexes are described, and their resulting interlocked assets are discussed in relationship with the very specific properties of water as a solvent.
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Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2958-2964
DOI: 10.1039/C4OB02284J, PaperYuanxiang Wang, Brendan Frett, Nick McConnell, Hong-yu Li
The first example of metal-free regioselective hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate is accomplished.
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Primary amine recognition in water by a calix[6]aza-cryptand incorporated in dodecylphosphocholine micelles

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2931-2938
DOI: 10.1039/C4OB02495H, PaperEmilio Brunetti, Alex Inthasot, Flore Keymeulen, Olivia Reinaud, Ivan Jabin, Kristin Bartik
A zinc calix[6]azacryptand complex was incorporated into dodecylphosphocholine micelles. This complex can strongly and selectively bind linear primary amines in an aqueous medium.
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Total synthesis of a thromboxane receptor antagonist, terutroban

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2951-2957
DOI: 10.1039/C4OB02302A, PaperWasim Ahmed, Prathama S. Mainkar, Srihari Pabbaraja, Srivari Chandrasekhar
Synthesis of terutroban (2) is achieved following a non-Diels-Alder approach using cost-effective chemicals.
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Recognition of bio-relevant dicarboxylate anions by an azacalix[2]arene[2]triazine derivative decorated with urea moieties

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,3070-3085
DOI: 10.1039/C4OB02283A, PaperMiguel M. Santos, Igor Marques, Silvia Carvalho, Cristina Moiteiro, Vitor Felix
The binding affinity of a dichlorocalix[2]arene[2]triazine based bis-urea azamacrocycle was investigated towards a wide range of bio-relevant dicarboxylate anions by a combination of 1H NMR titrations in CDCl3 and molecular dynamics simulations.
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Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2870-2874
DOI: 10.1039/C4OB02203C, CommunicationM. Bakthadoss, D. Kannan, J. Srinivasan, V. Vinayagam
A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction strategy.
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Molecular motion of donor-acceptor catenanes in water

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, 13,2927-2930
DOI: 10.1039/C4OB02457E, PaperFabien B. L. Cougnon, Nandhini Ponnuswamy, G. Dan Pantos, Jeremy K. M. Sanders
In this article, we use 1H NMR spectroscopy to study the spontaneous molecular motion of donor-acceptor [2]catenanes in water.
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