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Kathiravan, S. & Nicholls, I. A. (2019). Cobalt-Catalyzed Oxidative Annulation of Berizothiophene-[b]-1,1-dioxide through Diastereoselective Double C-H Activation. Organic Letters, 21(24), 9806-9811
Open this publication in new window or tab >>Cobalt-Catalyzed Oxidative Annulation of Berizothiophene-[b]-1,1-dioxide through Diastereoselective Double C-H Activation
2019 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, no 24, p. 9806-9811Article in journal (Refereed) Published
Abstract [en]

The use of inexpensive base metal catalysis to perform C H activation is an active field of research in organic synthesis. Described herein is a sustainable cobaltcatalyzed diastereoselective oxidative annulation/double C H activation of benzothiophene-[b]-1,1-dioxide with aminoquinolinamides under mild reaction conditions for the synthesis of annulated benzothiophenes.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-91026 (URN)10.1021/acs.orglett.9b03158 (DOI)000504805500002 ()31651175 (PubMedID)
Available from: 2020-01-20 Created: 2020-01-20 Last updated: 2020-01-20Bibliographically approved
Kathiravan, S., Suriyanarayanan, S. & Nicholls, I. A. (2019). Electrooxidative Amination of sp2 C–H Bonds: Coupling of Amines with Aryl Amides via Copper Catalysis. Organic Letters, 21(7), 1968-1972
Open this publication in new window or tab >>Electrooxidative Amination of sp2 C–H Bonds: Coupling of Amines with Aryl Amides via Copper Catalysis
2019 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, no 7, p. 1968-1972Article in journal (Refereed) Published
Abstract [en]

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis. However, the use of C−H activation for sp2 C−N bond formation remains one of the major challenges in the field of crosscoupling chemistry. Described herein is the first example of the synergistic combination of copper catalysis and electrocatalysis for aryl C−H amination under mild reaction conditions in an atom-and step-economical manner with the liberation of H2 as the sole and benign byproduct.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-81882 (URN)10.1021/acs.orglett.9b00003 (DOI)000464247500007 ()30785289 (PubMedID)2-s2.0-85062334838 (Scopus ID)
Available from: 2019-04-12 Created: 2019-04-12 Last updated: 2019-08-29Bibliographically approved
Nilsson, S. M. E., Suriyanarayanan, S., Kathiravan, S., Yli-Kauhaluoma, J., Kotiaho, T. & Nicholls, I. A. (2019). Enantioselective hyperporous molecularly imprinted thin film polymers. RSC Advances, 9(58), 33653-33656
Open this publication in new window or tab >>Enantioselective hyperporous molecularly imprinted thin film polymers
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2019 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 9, no 58, p. 33653-33656Article in journal (Refereed) Published
Abstract [en]

Significant enantioselective recognition has been achieved through the introduction of long range ordered and highly interconnected 300 nm diameter pores in molecularly imprinted polymer matrices.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019
National Category
Polymer Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-90327 (URN)10.1039/c9ra07425b (DOI)000496137600012 ()
Available from: 2019-11-29 Created: 2019-11-29 Last updated: 2019-11-29Bibliographically approved
Mahajan, R., Rouhi, M., Shinde, S., Bedwell, T., Incel, A., Mavliutova, L., . . . Sellergren, B. (2019). Highly Efficient Synthesis and Assay of Protein-Imprinted Nanogels by Using Magnetic Templates. Angewandte Chemie International Edition, 58(3), 727-730
Open this publication in new window or tab >>Highly Efficient Synthesis and Assay of Protein-Imprinted Nanogels by Using Magnetic Templates
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 3, p. 727-730Article in journal (Refereed) Published
Abstract [en]

We report an approach integrating the synthesis of protein-imprinted nanogels ("plastic antibodies") with a highly sensitive assay employing templates attached to magnetic carriers. The enzymes trypsin and pepsin were immobilized on amino-functionalized solgel-coated magnetic nanoparticles (magNPs). Lightly crosslinked fluorescently doped polyacrylamide nanogels were subsequently produced by high-dilution polymerization of monomers in the presence of the magNPs. The nanogels were characterised by a novel competitive fluorescence assay employing identical protein-conjugated nanoparticles as ligands to reversibly immobilize the corresponding nanogels. Both nanogels exhibited K-d<10 pM for their respective target protein and low cross-reactivity with five reference proteins. This agrees with affinities reported for solid-phase-synthesized nanogels prepared using low-surface-area glass-bead supports. This approach simplifies the development and production of plastic antibodies and offers direct access to a practical bioassay.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019
Keywords
competitive assays, molecularly imprinted polymers, nanogel synthesis, plastic antibodies
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-79846 (URN)10.1002/anie.201805772 (DOI)000455033700009 ()30308085 (PubMedID)2-s2.0-85056479757 (Scopus ID)
Funder
Knowledge Foundation, 20150086Knowledge Foundation, 20170059Swedish Research Council, 2014-4573
Note

Also funded by: Marie Sklodowska-Curie Actions (H2020-MSCA-ITN-2016)  -  722171-Biocapture

Available from: 2019-01-24 Created: 2019-01-24 Last updated: 2019-08-29Bibliographically approved
Suriyanarayanan, S., Olsson, G. D., Kathiravan, S., Ndizeye, N. & Nicholls, I. A. (2019). Non-Ionic Deep Eutectic Liquids: Acetamide-Urea Derived Room Temperature Solvents. International Journal of Molecular Sciences, 20(12), Article ID 2857.
Open this publication in new window or tab >>Non-Ionic Deep Eutectic Liquids: Acetamide-Urea Derived Room Temperature Solvents
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2019 (English)In: International Journal of Molecular Sciences, ISSN 1422-0067, E-ISSN 1422-0067, Vol. 20, no 12, article id 2857Article in journal (Refereed) Published
Abstract [en]

A family of non-ionic deep eutectic liquids has been developed based upon mixtures of solid N-alkyl derivatives of urea and acetamide that in some cases have melting points below room temperature. The eutectic behaviour and physical characteristics of a series of eleven eutectic mixtures are presented, along with a molecular dynamics study-supported hypothesis for the origin of the non-ideal mixing of these substances. Their use as solvents in applications ranging from natural product extraction to organic and polymer synthesis are demonstrated.

Place, publisher, year, edition, pages
MDPI, 2019
Keywords
deep-eutectic solvent, flickering cluster, acetamide-urea
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-86961 (URN)10.3390/ijms20122857 (DOI)000473756000007 ()31212745 (PubMedID)2-s2.0-85068473566 (Scopus ID)
Available from: 2019-07-23 Created: 2019-07-23 Last updated: 2019-08-29Bibliographically approved
Ndizeye, N., Suriyanarayanan, S. & Nicholls, I. A. (2019). Polymer synthesis in non-ionic deep eutectic solvents. Polymer Chemistry, 10(39), 5289-5295
Open this publication in new window or tab >>Polymer synthesis in non-ionic deep eutectic solvents
2019 (English)In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 10, no 39, p. 5289-5295Article in journal (Refereed) Published
Abstract [en]

Herein, we report the use of the use of non-ionic deep eutectic solvents (ni-DESs) as porogens in polymer synthesis. Three ni-DES systems, acetamide-N-methylacetamide (AA-NMA), N-methylacetamide-N-methylurea (NMA-NMU) and N-methylacetamide-N,N'-dimethylurea (NMA-NN'DMU), were deployed in the synthesis of a series of cross-linked copolymer monoliths comprised of a functional monomer, methacrylic acid (MAA) or hydroxyethylmethacrylate (HEMA), and a cross-linking monomer, ethylene glycol dimethylacrylate (EGDMA) or divinylbenzene (DVB) or 1,4-bis(acryloyl)piperazine (BAP). Polymers were synthesized under thermally initiated conditions with 2,2'-azobis(2-methylpropionitrile) (AIBN) or 2,2'-azobis(2-amidinopropane) dihydrochloride (ABAH) as an initiator. The resulting polymer monoliths were ground and sieved to yield particles of 63-125 mu m. Corresponding polymers prepared in conventional porogens, acetonitrile, toluene and water were synthesized to serve as controls. The influence of the respective niDESs on polymer morphologies was examined by Brunauer-Emmett-Teller (BET) N2-adsorption, Fourier transform infrared spectroscopy (FT-IR), elemental analysis, scanning electron microscopy (SEM) and zeta potential measurements. The materials displayed surface areas, pore volumes and pore diameters of 115-532 m(2) g(-1), 0.1-1.4 cm(3) g(-1) and 5.2-12.5 nm, generally comparable with those of polymers obtained using conventional solvents, thus presenting these ni-DESs as viable alternatives to conventional organic solvents. The post-polymerization recovery of the ni-DESs (>80%) was demonstrated, highlighting the potential for using these novel liquids as alternatives to conventional, and often more expensive, toxic, flammable or volatile solvents in polymer synthesis.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019
National Category
Polymer Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-89808 (URN)10.1039/c9py01039d (DOI)000489265500013 ()
Available from: 2019-10-25 Created: 2019-10-25 Last updated: 2019-10-25Bibliographically approved
Giovannoli, C., Passini, C., Di Nardo, F., Anfossi, L., Baggiani, C. & Nicholls, I. A. (2018). Affinity Capillary Electrochromatography of Molecularly Imprinted Thin Layers Grafted onto Silica Capillaries Using a Surface-Bound Azo-Initiator and Living Polymerization. Polymers, 10(2), Article ID 192.
Open this publication in new window or tab >>Affinity Capillary Electrochromatography of Molecularly Imprinted Thin Layers Grafted onto Silica Capillaries Using a Surface-Bound Azo-Initiator and Living Polymerization
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2018 (English)In: Polymers, ISSN 2073-4360, E-ISSN 2073-4360, Vol. 10, no 2, article id 192Article in journal (Refereed) Published
Abstract [en]

Molecularly imprinted thin layers were prepared in silica capillaries by using two different surface polymerization strategies, the first using 4,4-azobis(4-cyanovaleric acid) as a surface-coupled radical initiator, and the second, S-carboxypropyl-S'-benzyltrithiocarbonate as a reversible addition-fragmentation chain transfer (RAFT) agent in combination with 2,2-azobisisobutyronitrile as a free radical initiator. The ability to generate imprinted thin layers was tested on two different polymerization systems: (i) a 4-vinylpyridine/ethylene dimethacrylate (4VP-EDMA) in methanol-water solution with 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) as a template; and (ii) methacrylic acid/ethylene dimethacrylate (MAA-EDMA) in a chloroform solution with warfarin as the template molecule. The binding properties of the imprinted capillaries were studied and compared with those of the corresponding non-imprinted polymer coated capillaries by injecting the template molecule and by measuring its migration times relative to a neutral and non-retained marker. The role of running buffer hydrophobicity on recognition was investigated by studying the influence of varying buffer acetonitrile concentration. The 2,4,5-T-imprinted capillary showed molecular recognition based on a reversed phase mechanism, with a decrease of the template recognition in the presence of higher acetonitrile content; whereas warfarin-imprinted capillaries showed a bell-shaped trend upon varying the acetonitrile percentage, illustrating different mechanisms underlying imprinted polymer-ligand recognition. Importantly, the results demonstrated the validity of affinity capillary electrochromatography (CEC) to screen the binding properties of imprinted layers.

Place, publisher, year, edition, pages
MDPI, 2018
Keywords
molecularly imprinted polymers, capillary electrophoresis, controlled/living radical polymerization, 2, 4, 5-trichlorophenoxyacedic acid, warfarin
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-72298 (URN)10.3390/polym10020192 (DOI)000427542900087 ()2-s2.0-85042197819 (Scopus ID)
Available from: 2018-04-10 Created: 2018-04-10 Last updated: 2019-08-29Bibliographically approved
Mandal, S., Suriyanarayanan, S., Nicholls, I. A. & Ramanujam, K. (2018). Electrochemically synthesized molecularly imprinted polyaniline nanostructure: A recognition matrix for biotinylated targets. Paper presented at 255th National Meeting and Exposition of the American-Chemical-Society (ACS) - Nexus of Food, Energy, and Water, MAR 18-22, 2018, New Orleans, LA. Abstract of Papers of the American Chemical Society, 255
Open this publication in new window or tab >>Electrochemically synthesized molecularly imprinted polyaniline nanostructure: A recognition matrix for biotinylated targets
2018 (English)In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 255Article in journal, Meeting abstract (Other academic) Published
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2018
National Category
Chemical Sciences
Research subject
Natural Science, Chemistry
Identifiers
urn:nbn:se:lnu:diva-76897 (URN)000435537700366 ()
Conference
255th National Meeting and Exposition of the American-Chemical-Society (ACS) - Nexus of Food, Energy, and Water, MAR 18-22, 2018, New Orleans, LA
Available from: 2018-07-17 Created: 2018-07-17 Last updated: 2018-07-17Bibliographically approved
Ndizeye, N., Suriyanarayanan, S. & Nicholls, I. A. (2018). Hierarchical polymeric architectures through molecular imprinting in liquid crystalline environments. European Polymer Journal, 106, 223-231
Open this publication in new window or tab >>Hierarchical polymeric architectures through molecular imprinting in liquid crystalline environments
2018 (English)In: European Polymer Journal, ISSN 0014-3057, E-ISSN 1873-1945, Vol. 106, p. 223-231Article in journal (Refereed) Published
Abstract [en]

The use of liquid crystalline (LC) media as sacrificial templates during the polymer synthesis has been explored. The LC-media introduce morphological features into resultant polymers which when used together with molecular imprinting can produce materials with hierarchical architectures. Bupivacaine (1) imprinted co-polymers of 2-hydroxyethylmethacrylate (HEMA) (2a) and 1,4-divinylbenzene (DVB) (3a) were synthesized using photochemical initiation in lyotrophic liquid crystalline phases of AOT (5) in water/p-xylene and Triton X-100 (6) /water systems. SEM studies revealed the impact of the LC-media on polymer morphology, with polymer brush-like structures, with bristles of ≈30 nm diameter. The polymer morphology reflects that of the hexagonal phase of the LC medium. The rebinding characteristics of polymer films were evaluated quartz crystal microbalance (QCM, under FIA conditions). The influence of the presence of imprinting-derived recognition sites in AOT (5) in water/p-xylene polymer film induced brush-like features which provided a 25-fold enhancement of sensor sensitivity. This chemosensor was shown to be selective for the local anesthetic template, bupivacaine, through studies using the structural analogues ropivacaine and mepivacaine.

Place, publisher, year, edition, pages
Elsevier, 2018
Keywords
Bupivacaine, liquid crystalline medium, molecularly imprinted polymer, nanostructured polymer films, piezoelectric sensor, quartz crystal microbalance
National Category
Polymer Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-78287 (URN)10.1016/j.eurpolymj.2018.07.036 (DOI)000445993400027 ()2-s2.0-85050408593 (Scopus ID)
Available from: 2018-10-11 Created: 2018-10-11 Last updated: 2019-08-29Bibliographically approved
Mandal, S., Suriyanarayanan, S., Nicholls, I. A. & Ramanujam, K. (2018). Selective Sensing of the Biotinyl Moiety Using Molecularly Imprinted Polyaniline Nanowires. Journal of the Electrochemical Society, 165(14), B669-B678
Open this publication in new window or tab >>Selective Sensing of the Biotinyl Moiety Using Molecularly Imprinted Polyaniline Nanowires
2018 (English)In: Journal of the Electrochemical Society, ISSN 0013-4651, E-ISSN 1945-7111, Vol. 165, no 14, p. B669-B678Article in journal (Refereed) Published
Abstract [en]

A chemosensor for selective recognition of biotinyl moiety has been devised using electropolymerized film and tested against selective biotinylated targets. The sensor comprises biotin molecularly imprinted polymer (MIP) polymeric nanowires, as a recognition element, overlaid on gold-coated quartz transducers. The preparation of nanostructured MIPs and reference systems have been demonstrated using electrochemical copolymerization of the stabilized complex between the template (biotin), the functional monomer (4-aminobenzoic acid), and cross-linker (aniline) and/or sacrificial biotin-modified Al2O3 membrane. Density functional theoretical studies signify formation of a stable hydrogen-bonded complex of biotin with 4-aminobenzoic acid in the pre-polymerization mixture. Scanning electron microscope studies revealed uniformly grown and densely packed polyaniline hierarchical structures. Piezoelectric microgravimetry under flow injection analysis (FIA) conditions revealed selective binding of biotin methyl ester (BtOMe, 4) (79.89 +/- 2.17 Hz/mM) with imprinted polyaniline hierarchical structures over 10 fold higher than the non-imprinted counterpart. The detection limit of the MIP is 50 nM under optimized conditions. Particularly, the sensor selectively recognizes BtOMe from structural or functional analogues, such as thiamine (4.87 +/- 0.10 Hz/mM) and pyridoxamine (12.08 +/- 0.24 Hz/mM). Importantly, the MIP hierarchical structures were shown to be selective for biotinylated targets (biotin moiety labeled cytochrome C, dextran, oxytocin and obestatin). (C) 2018 The Electrochemical Society.

Place, publisher, year, edition, pages
Electrochemical Society, 2018
National Category
Biochemistry and Molecular Biology Biophysics
Research subject
Chemistry, Biochemistry
Identifiers
urn:nbn:se:lnu:diva-78608 (URN)10.1149/2.0401814jes (DOI)000447842800001 ()2-s2.0-85067498186 (Scopus ID)
Available from: 2018-11-02 Created: 2018-11-02 Last updated: 2019-08-29Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-0407-6542

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