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Effect of ligand sequence-specific modification on DNA hybrid catalysisElectronic supplementary information (ESI) available: Experimental section, copies of 1H and 13C NMR spectra and HRMS for selected compounds, HPLC analysis of products, basic spectra for CD and UV-vis titration data. See DOI: 10.1039/c7ob01249g (English)

In: Organic & biomolecular chemistry   ;  15 ,  32  ;  2017
  • ISSN:
    1477-0520
  • Article (Journal)  /  Print

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Development of a stereoselective asymmetric catalytic system with high conversion is the key to success for acquiring chiral materials. In recent years, DNA hybrid catalysts have attracted significant interest due to their excellent abilities in accelerating reactions and achieving high enantioselectivity. We report here that bipyridine linked with polyamide as a sequence-specific catalytic ligand was designed to perform a DNA hybrid asymmetric reaction. The products presented different stereoselectivities compared to the results of reactions catalyzed by bipyridine. Comparing catalytic experiments based on alternative oligonucleotides verified that sequence-locating of the ligand affected the catalytic microenvironment. Circular dichroism spectra, combined with singular value decomposition, proposed that different binding modes could exist somewhere between the ligand and alternative sequences. The current work provides a strategy to extend the chemical range of DNA-based catalysis. We report a sequence-specific catalytic ligand as a chemical modification strategy to achieve DNA-based asymmetric reactions with sequence-dependent enantioselectivity.

Table of contents – Volume 15, Issue 32

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The tables of contents are generated automatically and are based on the data records of the individual contributions available in the index of the TIB portal. The display of the Tables of Contents may therefore be incomplete.

68
Calcium carbide catalytically activated with tetra-n-butyl ammonium fluoride for Sonogashira cross coupling reactionsElectronic supplementary information (ESI) available: Supplementary tables, experimental procedures, characterization data, and copies of 1H and 13C NMR spectra. See DOI: 10.1039/c7ob01334e
Hosseini, Abolfazl et al. | 2017
671
Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detectionElectronic supplementary information (ESI) available: Synthesis of alkyne-derivatized thiazole orange 1, additional 1H NMR spectra, ESI-MS, HPLC traces and fluorescence data. See DOI: 10.1039/c7ob01592e
Gahtory, Digvijay et al. | 2017
672
Effect of spermine-derived AGEs on oxidative stress and polyamine metabolismElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01346a
Tsutsui, Ayumi et al. | 2017
672
Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequenceElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01536d
Nakamura, Akira et al. | 2017
676
Proof of principle of a three-input AND-INHIBIT-OR combinatorial logic gate arrayElectronic supplementary information (ESI) available: Synthetic details, UV-vis absorption, 1H & 13C NMR, IR and mass spectra. See DOI: 10.1039/c7ob01223c
Magri, David C et al. | 2017
678
A facile I2-catalyzed synthesis of imidazo[1,2-a]pyridines via sp3 C-H functionalization of azaarenes and evaluation of anticancer activityElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01384a
Mani, Geeta Sai et al. | 2017
688
Synthesis of dibenzo[a,c]carbazoles from 2-(2-halophenyl)-indoles and iodobenzenes via palladium-catalyzed dual C-H functionalizationElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01638g
Wu, Lijun et al. | 2017
6683
Front cover
| 2017
6685
Contents list
| 2017
6692
Fluorescent probes for hydrogen polysulfides (H2Sn, n > 1): from design rationale to applications
Gupta, Neha / Reja, Shahi Imam / Bhalla, Vandana / Kumar, Manoj et al. | 2017
6702
Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence
Nakamura, Akira / Tanaka, Satoshi / Imamiya, Akira / Takane, Reo / Ohta, Chiaki / Fujimura, Kazuma / Maegawa, Tomohiro / Miki, Yasuyoshi et al. | 2017
6706
Proof of principle of a three-input AND–INHIBIT–OR combinatorial logic gate array
Magri, David C. / Spiteri, Jake C. et al. | 2017
6710
Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection
Gahtory, Digvijay / Murtola, Merita / Smulders, Maarten M. J. / Wennekes, Tom / Zuilhof, Han / Strömberg, Roger / Albada, Bauke et al. | 2017
6715
Metal-free radical aromatic carbonylations mediated by weak basesElectronic supplementary information (ESI) available: Experimental procedures, analytical data of all new compounds. See DOI: 10.1039/c7ob01572k
Koziakov, Denis et al. | 2017
6715
Metal-free radical aromatic carbonylations mediated by weak bases
Koziakov, Deni / Jacobi von Wangelin, Axel et al. | 2017
6720
Effect of spermine-derived AGEs on oxidative stress and polyamine metabolism
Tsutsui, Ayumi / Pradipta, Ambara R. / Kitazume, Shinobu / Taniguchi, Naoyuki / Tanaka, Katsunori et al. | 2017
6725
Supramolecular control of heme binding and electronic states in multi-heme peptide assemblies
Christopher Fry, H. / Wood, Anna R. / Solomon, Lee A. et al. | 2017
6731
Nucleophile dependent formation of 6- and 7-membered N-heterocycles by platinum-catalysed cyclisation of 1,5-bisallenes
Quirós, María Teresa / Hurtado-Rodrigo, César / Muñoz, María Paz et al. | 2017
6731
Nucleophile dependent formation of 6- and 7-membered N-heterocycles by platinum-catalysed cyclisation of 1,5-bisallenesElectronic supplementary information (ESI) available: Experimental details, characterisation of compounds, full kinetic analysis and NMR spectra. See DOI: 10.1039/c7ob01469d
Quirós, María Teresa et al. | 2017
6738
Effect of ligand sequence-specific modification on DNA hybrid catalysis
Zhou, H. / Chen, D. / Bai, J. K. / Sun, X. L. / Li, C. / Qiao, R. Z. et al. | 2017
6738
Effect of ligand sequence-specific modification on DNA hybrid catalysisElectronic supplementary information (ESI) available: Experimental section, copies of 1H and 13C NMR spectra and HRMS for selected compounds, HPLC analysis of products, basic spectra for CD and UV-vis titration data. See DOI: 10.1039/c7ob01249g
Zhou, H et al. | 2017
6746
Nonlinear effects at the soft interface of an emulsion in the List–Lerner–Barbas aldol reaction
Dutta, Jyoti / Wakdikar, Nutan / Tiwari, Shraeddha et al. | 2017
6746
Nonlinear effects at the soft interface of an emulsion in the List-Lerner-Barbas aldol reactionElectronic supplementary information (ESI) available: Experimental details, NMR data, details of HPLC analysis and representative CD spectra. See DOI: 10.1039/c7ob01576c
Dutta, Jyoti et al. | 2017
6753
Efficient active-template synthesis of calix[6]arene-based oriented pseudorotaxanes and rotaxanesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01642e
Zanichelli, Valeria et al. | 2017
6753
Efficient active-template synthesis of calix[6]arene-based oriented pseudorotaxanes and rotaxanes
Zanichelli, Valeria / Ragazzon, Giulio / Orlandini, Guido / Venturi, Margherita / Credi, Alberto / Silvi, Serena / Arduini, Arturo / Secchi, Andrea et al. | 2017
6764
Amide rotation trajectories probed by symmetry
Kubyshkin, Vladimir / Budisa, Nediljko et al. | 2017
6764
Amide rotation trajectories probed by symmetryThe article is dedicated to the memory of Prof. Yuriy Kholin (1962-2017), who nurtured a generation of young talented Ukrainian chemists.Electronic supplementary information (ESI) available: Tables S1-S5, copies of the NMR spectra for compounds. CCDC 1554475 and 1554476. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob01421j
Kubyshkin, Vladimir et al. | 2017
6773
Self-assembly of an amphipathic ααβ-tripeptide into cationic spherical particles for intracellular delivery
Bucci, Raffaella / Das, Priyadip / Iannuzzi, Filomena / Feligioni, Marco / Gandolfi, Raffaella / Gelmi, Maria Luisa / Reches, Meital / Pellegrino, Sara et al. | 2017
6773
Self-assembly of an amphipathic aab-tripeptide into cationic spherical particles for intracellular delivery
Bucci, R. / Das, P. / Iannuzzi, F. / Feligioni, M. / Gandolfi, R. / Gelmi, M. / Reches, M. / Pellegrino, S. et al. | 2017
6773
Self-assembly of an amphipathic ααβ-tripeptide into cationic spherical particles for intracellular deliveryElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01693j
Bucci, Raffaella et al. | 2017
6780
A facile I2-catalyzed synthesis of imidazo[1,2-a]pyridines via sp3 C–H functionalization of azaarenes and evaluation of anticancer activity
Mani, Geeta Sai / Shaik, Siddiq Pasha / Tangella, Yellaiah / Bale, Swarna / Godugu, Chandraiah / Kamal, Ahmed et al. | 2017
6792
Insights into the role of 3-O-sulfotransferase in heparan sulfate biosynthesisElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01533j
Meneghetti, Maria Cecília Zorél et al. | 2017
6792
Insights into the role of 3-O-sulfotransferase in heparan sulfate biosynthesis
Meneghetti, Maria Cecília Zorél / Gesteira Ferreira, Tarsi / Tashima, Alexandre Keiji / Chavante, Suely F. / Yates, Edwin Alexander / Liu, Jian / Nader, Helena Bonciani / Lima, Marcelo A. et al. | 2017
6800
Calcium carbide catalytically activated with tetra-n-butyl ammonium fluoride for Sonogashira cross coupling reactions
Hosseini, Abolfazl / Pilevar, Afsaneh / Hogan, Eimear / Mogwitz, Bori / Schulze, Anne S. / Schreiner, Peter R. et al. | 2017
6808
Synthesis of dibenzo[a,c]carbazoles from 2-(2-halophenyl)-indoles and iodobenzenes via palladium-catalyzed dual C–H functionalization
Wu, Lijun / Deng, Guobo / Liang, Yun et al. | 2017
6813
Dissociation of Mg(ii) and Zn(ii) complexes of simple 2-oxocarboxylates – relationship to CO2 fixation, and the Grignard and Barbier reactions
Miller, Glenn B. S. / Uggerud, Einar et al. | 2017
6813
Dissociation of Mg(ii) and Zn(ii) complexes of simple 2-oxocarboxylates - relationship to CO2 fixation, and the Grignard and Barbier reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01327b
Miller, Glenn B. S et al. | 2017
6826
Synthesis and conformational analysis of peptides embodying 2,3-methanopipecolic acids
Ricci, Luciano / Sernissi, Lorenzo / Scarpi, Dina / Bianchini, Francesca / Contini, Alessandro / Occhiato, Ernesto G. et al. | 2017
6826
Synthesis and conformational analysis of peptides embodying 2,3-methanopipecolic acidsElectronic supplementary information (ESI) available: Experimental procedures, characterization data and NMR spectra of all new compounds, computational calculations and biological assays. See DOI: 10.1039/c7ob01617d
Ricci, Luciano et al. | 2017
6837
An efficient one-pot approach for the regio- and diastereoselective synthesis of trans-dihydrofuran derivatives: cytotoxicity and DNA-binding studies
Tangella, Yellaiah / Manasa, Kesari Lakshmi / Laxma Nayak, V. / Sathish, Manda / Sridhar, B. / Alarifi, Abdullah / Nagesh, Narayana / Kamal, Ahmed et al. | 2017
6837
An efficient one-pot approach for the regio- and diastereoselective synthesis of trans-dihydrofuran derivatives: cytotoxicity and DNA-binding studiesElectronic supplementary information (ESI) available: Crystallographic data and 1H and 13C spectra of all the synthesized compounds. CCDC 1524575. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ob01456b
Tangella, Yellaiah et al. | 2017
6855
Back cover
| 2017
Supramolecular control of heme binding and electronic states in multi-heme peptide assembliesElectronic supplementary information (ESI) available: Materials and methods, additional UV/visible, CD, FTIR, and AFM data. See DOI: 10.1039/c7ob01081h
Christopher Fry, H et al. | 2017

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