Royal Society of Chemistry

Synthesis of labile all-trans-7,8,7[prime or minute],8[prime or minute]-bis-acetylenic carotenoids by bi-directional Horner-Wadsworth-Emmons condensation

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02144D, PaperBelen Vaz, Noelia Fontan, Marta Castineira, Rosana Alvarez, Angel R. de Lera
Two symmetrical C7,C8-acetylenic carotenoids have been stereoselectively prepared using a bi-directional Horner-Wadsworth-Emmons condensation of the C10-dialdehyde and C15-phosphonates.
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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

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Reaction of [small beta]-enaminones and acetylene dicarboxylates: synthesis of substituted 1,2-dihydropyridinones

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Synthesis of directly fused porphyrin dimers through Fe(OTf)3-mediated oxidative coupling

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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A [gamma]-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Gas phase chemistry of N-benzylbenzamides with silver(I) cations: characterization of benzylsilver cation

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Validating the alkene and alkyne hydrophosphonylation as an entry to organophosphonates

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02501F, PerspectiveAlessandro Dondoni, Alberto Marra
The hydrophosphonylation of terminal alkenes and alkynes by H-phosphonates affords Markovnikov and/or anti-Markovnikov adducts depending on the catalyst (a metal or a radical initiator) and the reaction conditions.
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Solid-state circularly polarised luminescence of atropisomeric fluorophores embedded in achiral myo-inositol-containing polyurethanes

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
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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Identification of benzenesulfonamide quinoline derivatives as potent HIV-1 replication inhibitors targeting Rev protein

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1792-1799
DOI: 10.1039/C4OB02247E, PaperFudi Zhong, Guannan Geng, Bing Chen, Ting Pan, Qianwen Li, Hui Zhang, Chuan Bai
A benzenesulfonamide quinoline compound with potent anti-HIV-1 replication activity and low toxicity by targeting HIV-1 Rev protein was identified with high-throughput screening and SAR studies.
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Cyclodextrin- and calixarene-based polycationic amphiphiles as gene delivery systems: a structure-activity relationship study

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1708-1723
DOI: 10.1039/C4OB02204A, PaperLaura Gallego-Yerga, Michela Lomazzi, Valentina Franceschi, Francesco Sansone, Carmen Ortiz Mellet, Gaetano Donofrio, Alessandro Casnati, Jose M. Garcia Fernandez
Multi-head/multi-tail facial amphiphiles built on cyclodextrin (CD) and calixarene (CA) scaffolds are paradigmatic examples of monodisperse gene delivery systems.
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Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1647-1653
DOI: 10.1039/C4OB02251C, PaperMutsumi Kobayashi, Mei Takatsuka, Ryo Sekiya, Takeharu Haino
Calix[4]resorcinarene-based cavitand recognized the methyl group of the guests to form 1 : 1 host-guest complexes. In the solid state, the cavitand formed a dimeric capsule in which two molecules of nitromethane were entrapped by weak noncovalent interactions.
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Computational study on the intramolecular self-organization of the macrorings of some 'giant' cyclodextrins (CDn, n = 40, 70, 85, 100)

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1680-1689
DOI: 10.1039/C4OB02218A, PaperPetko M. Ivanov, Emanouil J. Atanassov, Carlos Jaime
A limited number of modes determine the overall deformations of the macrorings, which may have more than one cavity. Accordingly, they have the potential to accommodate more than one substrate molecule.
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Reactivity of aldehydes at the air-water interface. Insights from molecular dynamics simulations and ab initio calculations

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1673-1679
DOI: 10.1039/C4OB02029D, PaperMarilia T. C. Martins-Costa, Francisco F. Garcia-Prieto, Manuel F. Ruiz-Lopez
Computer simulations show that solvation effects at the air-water interface significantly influence the chemistry of aldehydes, enhancing for instance the benzaldehyde photolysis rate constant by one order of magnitude.
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UV-visible and 1H-15N NMR spectroscopic studies of colorimetric thiosemicarbazide anion sensors

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1662-1672
DOI: 10.1039/C4OB02091J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Kristina N. Farrugia, Damjan Makuc, Agnieszka Podborska, Konrad Szacilowski, Janez Plavec, David C. Magri
Four model thiosemicarbazide anion chemosensors containing three N-H bonds, substituted with phenyl and/or 4-nitrophenyl units, were synthesised and studied for their anion binding abilities with hydroxide, fluoride, acetate, dihydrogen phosphate and chloride.
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Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions

Org. and Biomol. Chem. - 31 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1624-1628
DOI: 10.1039/C4OB02324B, CommunicationRui Wang, John R. Falck
An efficient and asymmetric synthesis approach towards the biologically interesting molecule 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) was developed. This protocol mainly relied on our mild cross-coupling and asymmetric stannylation.
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