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A Bioluminescence Reporter Assay for Retinoic Acid Control of Translation of the GluR1 Subunit of the AMPA Glutamate Receptor (2019)
Journal Article
Khatib, T., Whiting, A., Chisholm, D. R., Redfern, C., Müller, B., & McCaffery, P. (2019). A Bioluminescence Reporter Assay for Retinoic Acid Control of Translation of the GluR1 Subunit of the AMPA Glutamate Receptor. Molecular Neurobiology, 56(10), 7074-7084. https://doi.org/10.1007/s12035-019-1571-9

Retinoic acid (RA) regulates numerous aspects of central nervous system function through modulation of gene transcription via retinoic acid receptors (RARs). However, RA has important roles independent of gene transcription (non-genomic actions) and... Read More about A Bioluminescence Reporter Assay for Retinoic Acid Control of Translation of the GluR1 Subunit of the AMPA Glutamate Receptor.

Photoactivated cell-killing involving a low molecular weight, donor-acceptor diphenylacetylene (2019)
Journal Article
Chisholm, D., Lamb, R., Pallett, T., Affleck, V., Holden, C., Marrison, J., …Ambler, C. A. (2019). Photoactivated cell-killing involving a low molecular weight, donor-acceptor diphenylacetylene. Chemical Science, 10(17), 4673-4683. https://doi.org/10.1039/c9sc00199a

Photoactivation of photosensitisers can be utilised to elicit the production of ROS, for potential therapeutic applications, including the destruction of diseased tissues and tumours. A novel class of photosensitiser, exemplified by DC324, has been d... Read More about Photoactivated cell-killing involving a low molecular weight, donor-acceptor diphenylacetylene.

Using Nature’s polyenes as templates: Studies of synthetic xanthomonadin analogues and realising their potential as antioxidants (2019)
Journal Article
Madden, K. S., Jokhoo, H., Conradi, F., Knowles, J., Mullineaux, C., & Whiting, A. (2019). Using Nature’s polyenes as templates: Studies of synthetic xanthomonadin analogues and realising their potential as antioxidants. Organic and Biomolecular Chemistry, 17(15), 3752-3759. https://doi.org/10.1039/c9ob00275h

Two truncated analogues of the polyenyl photoprotective xanthomonadin pigments have been synthesised utilising an iterative Heck-Mizoroki/iododeboronation cross coupling approach and investigated as models of the natural products as photoprotective a... Read More about Using Nature’s polyenes as templates: Studies of synthetic xanthomonadin analogues and realising their potential as antioxidants.

A solid-supported arylboronic acid catalyst for direct amidation (2019)
Journal Article
Du, Y., Barber, T., Lim, S. E., Rzepa, H. S., Baxendale, I. R., & Whiting, A. (2019). A solid-supported arylboronic acid catalyst for direct amidation. Chemical Communications, 55(20), 2916-2919. https://doi.org/10.1039/c8cc09913h

An efficient heterogeneous amidation catalyst has been prepared by co-polymerisation of styrene, DVB with 4-styreneboronic acid, which shows wide substrate applicability and higher reactivity than the equivalent homogeneous phenylboronic acid, sugges... Read More about A solid-supported arylboronic acid catalyst for direct amidation.

Fluorescent retinoic acid analogues as probes for biochemical and intracellular characterization of retinoid signalling pathways (2019)
Journal Article
Chisholm, D., Tomlinson, C., Zhou, G., Holden, C., Affleck, V., Lamb, R., …Pohl, E. (2019). Fluorescent retinoic acid analogues as probes for biochemical and intracellular characterization of retinoid signalling pathways. ACS Chemical Biology, 14(3), 369-377. https://doi.org/10.1021/acschembio.8b00916

Retinoids, such as all-trans-retinoic acid (ATRA), are endogenous signalling molecules derived from Vitamin A that influ-ence a variety of cellular processes through mediation of transcription events in the cell nucleus. Due to these wide-ranging and... Read More about Fluorescent retinoic acid analogues as probes for biochemical and intracellular characterization of retinoid signalling pathways.

A novel fluorescence competition assay for retinoic acid binding proteins (2018)
Journal Article
Tomlinson, C. W., Chisholm, D. R., Valentine, R., Whiting, A., & Pohl, E. (2018). A novel fluorescence competition assay for retinoic acid binding proteins. ACS Medicinal Chemistry Letters, 9(12), 1297–1300-1300. https://doi.org/10.1021/acsmedchemlett.8b00420

Vitamin A derived retinoid compounds have multiple, powerful roles in the cellular growth and development cycle, and as a result have attracted significant attention from both academic and pharmaceutical research in developing and characterizing synt... Read More about A novel fluorescence competition assay for retinoic acid binding proteins.

Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues (2018)
Journal Article
Madden, K., Laroche, B., David, S., Batsanov, A., Thompson, D., Knowles, J., & Whiting, A. (2018). Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues. European Journal of Organic Chemistry, 2018(38), 5312-5322. https://doi.org/10.1002/ejoc.201800540

A number of aryl building blocks for the synthesis of two xanthomonadin natural product pigments, as well as a related analogue, were accessed using a divergent hydroboration/bromoboration approach from a key alkynyl intermediate. A new approach towa... Read More about Approaches to Styrenyl Building Blocks for the Synthesis of Polyene Xanthomonadin and its Analogues.

Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX (2018)
Journal Article
Liu, S., Zhang, Q., Tian, X., Fan, S., Huang, J., & Whiting, A. (2018). Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX. Green Chemistry, 20(20), 4729-4737. https://doi.org/10.1039/c8gc02628a

The direct selective halogenation of unactivated C(sp3)–H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air.... Read More about Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX.

An accessible method for DFT calculation of 11B NMR shifts of organoboron compounds (2018)
Journal Article
Rzepa, H., Arkhipenko, S., Wang, E., Batsanov, A., Sabatini, M., Karaluka, V., …Sheppard, T. (2018). An accessible method for DFT calculation of 11B NMR shifts of organoboron compounds. Journal of Organic Chemistry, 83(15), 8020-8025. https://doi.org/10.1021/acs.joc.8b00859

The study of boron-mediated reactions in organic synthesis and reactions of organoboron compounds is greatly facilitated by the use of 11B NMR. However, the identification and characterisation of reaction intermediates in often complex systems is far... Read More about An accessible method for DFT calculation of 11B NMR shifts of organoboron compounds.

A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines (2018)
Journal Article
Eberlin, L., Macé, A., Batsanov, A., Carboni, B., & Whiting, A. (2018). A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines. ChemistrySelect, 3(16), 4557-4561. https://doi.org/10.1002/slct.201800945

A new cascade reaction to access C‐pyrrolyl nitrones en route to isoxazolidines is reported; a process that involves four successive steps, the first key step being an ene‐reaction of a 3‐methyl‐1,3‐dienylboronate ester with an aryl nitroso compounds... Read More about A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines.

Probing biological activity through structural modelling of ligand-receptor interactions of 2,4-disubstituted thiazole retinoids (2018)
Journal Article
Haffez, H., Chisholm, D., Tatum, N., Valentine, R., Redfern, C., Pohl, E., …Przyborski, S. (2018). Probing biological activity through structural modelling of ligand-receptor interactions of 2,4-disubstituted thiazole retinoids. Bioorganic and Medicinal Chemistry, 26(8), 1560-1572. https://doi.org/10.1016/j.bmc.2018.02.002

Retinoids, such as all-trans-retinoic acid (ATRA), regulate cellular differentiation and signalling pathways in chordates by binding to nuclear retinoic acid receptors (RARα/β/γ). Polar interactions between receptor and ligand are important for bindi... Read More about Probing biological activity through structural modelling of ligand-receptor interactions of 2,4-disubstituted thiazole retinoids.

Mechanistic insights into boron-catalysed direct amidation reactions (2018)
Journal Article
Arkhipenko, S., Batsanov, A., Sabatini, M., Karaluka, V., Sheppard, T., Rzepa, H., & Whiting, A. (2018). Mechanistic insights into boron-catalysed direct amidation reactions. Chemical Science, 9(4), 1058-1072. https://doi.org/10.1039/c7sc03595k

The generally accepted 'mechanism' of boron-catalysed direct amidation is brought into question in this study and new alternatives considered. The interactions of borinic acids and boronic acids separately with amines, carboxylic acids and mixutres o... Read More about Mechanistic insights into boron-catalysed direct amidation reactions.

Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations (2017)
Journal Article
Pujol, A., & Whiting, A. (2017). Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations. Journal of Organic Chemistry, 82(14), 7265-7279. https://doi.org/10.1021/acs.joc.7b00854

Homoallylic boronate carboxylate esters derived from unsaturated aldehydes via an imination, β-borylation, imine hydrolysis, and Wittig trapping sequence, were subjected to a second boryl addition to give 1,3-diborylated carboxylate esters. Control o... Read More about Double Diastereoselective Approach to Chiral syn- and anti-1,3-Diol Analogues through Consecutive Catalytic Asymmetric Borylations.

Neurogenesis in Response to Synthetic Retinoids at Different Temporal Scales (2017)
Journal Article
Haffez, H., Khatib, T., McCaffery, P., Przyborski, S., Redfern, C., & Whiting, A. (2018). Neurogenesis in Response to Synthetic Retinoids at Different Temporal Scales. Molecular Neurobiology, 55(3), 1942-1950. https://doi.org/10.1007/s12035-017-0440-7

All-trans retinoic acid (ATRA) plays key roles in neurogenesis mediated by retinoic acid receptors (RARs). RARs are important targets for the therapeutic regulation of neurogenesis but effective drug development depends on modelling-based strategies... Read More about Neurogenesis in Response to Synthetic Retinoids at Different Temporal Scales.

The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors (2017)
Journal Article
Haffez, H., Chisholm, D., Valentine, R., Pohl, E., Redfern, C., & Whiting, A. (2017). The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors. MedChemComm, 8(3), 578-592. https://doi.org/10.1039/c6md00680a

All-trans-retinoic acid (ATRA) and its synthetic analogues EC23 and EC19 direct cellular differentiation by interacting as ligands for the retinoic acid receptor (RARα, β and γ) family of nuclear receptor proteins. To date, a number of crystal struct... Read More about The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors.

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines (2016)
Journal Article
Chisholm, D., Zhou, G., Pohl, E., Valentine, R., & Whiting, A. (2016). Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines. Beilstein Journal of Organic Chemistry, 12, 1851-1862. https://doi.org/10.3762/bjoc.12.174

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisa... Read More about Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines.

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring (2016)
Journal Article
Chisholm, D. R., Valentine, R., Pohl, E., & Whiting, A. (2016). Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring. Journal of Organic Chemistry, 81(17), 7557-7565. https://doi.org/10.1021/acs.joc.6b01110

A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversio... Read More about Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring.

Alternative tandem cyclisation pathways in the reaction between imines and enones, (2016)
Journal Article
Girling, P., Batsanov, A., Calow, A., Shen, H., & Whiting, A. (2016). Alternative tandem cyclisation pathways in the reaction between imines and enones,. Tetrahedron, 72(8), 1105-1113. https://doi.org/10.1016/j.tet.2016.01.006

Dihydroisoquinoline reacts with Danishefsky's diene under Lewis acidic conditions or neat, to give low to moderate yields of the formal aza-Diels-Alder, [4+2]-cycloadduct. However, using methoxyvinyl methylketone with Lewis acid catalysis does not gi... Read More about Alternative tandem cyclisation pathways in the reaction between imines and enones,.

An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions (2015)
Journal Article
Chaiyaveij, D., Batsanov, A., Fox, M., Marder, T., & Whiting, A. (2015). An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions. Journal of Organic Chemistry, 80(19), 9518-9534. https://doi.org/10.1021/acs.joc.5b01470

Catalytic aerobic oxidation of phenyl hydroxycarbamate 1 and 1-hydroxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ, which were trapped in nitroso-Diels–Alder (NDA) reactions with various dienes to... Read More about An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions.