Browsing School of Chemistry (Scholarly Articles) by Author "Murphy, Paul V."
Now showing items 1-20 of 42
-
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol
Bennett, Jack; Murphy, Paul V. (MDPI, 2020-06-03)(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic ... -
Allylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugars
Moynihan, Lorna; Chadda, Rekha; McArdle, Patrick; Murphy, Paul V. (American Chemical Society, 2015-12-09)Allylic azide rearrangement is used. in,tandem with. intramolecular azide-alkene cycloaddition to give a triazoline that when subsequently decomposed in the presence of a nucleophile gives piperidines. The tandem reaction ... -
Allylic azide rearrangement in tandem with intramolecular Huisgen cycloaddition for iminosugar and glycomimetic synthesis. Functionalized piperidine, pyrrolidine and pyrrolotriazoles from D-mannose
Chadda, Rekha; McArdle, Patrick; Murphy, Paul V. (Thieme Publishing, 2017-04-20)Intramolecular Huisgen azide-alkene cycloaddition reaction of 7-azido-hepta-1,5-diene-3,4-diols, prepared from methyl α-d-mannopyranoside, were carried out. Allylic azide rearrangement to secondary azides occurred ... -
Anomer preferences for glucuronic and galacturonic acid and derivatives and influence of electron-withdrawing substituents
Kerins, Louise; Byrne, Sylvester; Gabba, Adele; Murphy, Paul V. (American Chemical Society, 2018-07-04)Equilibrium anomeric ratios are reported for pyranoses (hemiacetals) of glucuronic and galacturonic acid and their derivatives. These are compared to related gluco- and galactopyranoses and to deoxyfluorogluco- and ... -
Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins
Sabine André, Sabine; O'Sullivan, Shane; Koller, Christiane; Murphy, Paul V.; Gabius, Hans-Joachim (Royal Society of Chemistry, 2015-02-17)Emerging insights into the functional spectrum of tissue lectins leads to identification of new targets for the custom-made design of potent inhibitors, providing a challenge for synthetic chemistry. The affinity and ... -
Bi- to tetravalent glycoclusters: synthesis, structure-activity profiles as lectin inhibitors and impact of combining both valency and headgroup tailoring on selectivity.
Wang, Guan-Nan; Murphy, Paul V. (Royal Society of Chemistry, 2012-06-29)The emerging functional versatility of cellular glycans makes research on the design of synthetic inhibitors a timely topic. In detail, the combination of ligand (or headgroup or contact site) structure with spatial ... -
Building blocks from monosaccharides for synthesis of scaffolds, including macrocycles. Application of allylic azide rearrangement, azide-alkyne cycloaddition and ring closing metathesis
Fox, Karen A.; Chadda, Rekha; Cardona, Francisco; Barron, Stephen; McArdle, Patrick; Murphy, Paul V. (Elsevier, 2020-09-18)Synthesis of compounds with characteristics of natural products are required to increase the diversity and biological relevance of compounds for screening. These include new frameworks/scaffolds, with multiple stereogenic ... -
Coiled coil type neoglycoproteins presenting three lactose residues
Sweeney, Sinclair M.; Bullen, Gemma A.; Gillis, Richard B.; Adams, Gary G.; Rowe, Arthur J.; Harding, Stephen E.; Tucker, James H.R.; Peacock, Anna F.A.; Murphy, Paul V. (Elsevier, 2016-02-06)Scaffold design, synthesis and application are relevant for biomedical research. For example, multivalent interactions, such as those between cell surface glycoproteins and lectins can influence the potency and duration ... -
Combining glycocluster synthesis with protein engineering: an approach to probe into the significance of linker length in a tandem-repeat-type lectin (galectin-4)
Andre, Sabine; Wang, Guan-Nan; Gabius, Hans-Joachim; Murphy, Paul V. (Elsevier, 2014-05-07)Complementarity in lectin-glycan interactions in situ is assumed to involve spatial features in both the lectin and the glycan, giving a functional meaning to structural aspects of the lectin beyond its carbohydrate-binding ... -
Decorated macrocycles via ring-closing double-reductive amination. Identification of an apoptosis inducer of leukemic cells that at least partially antagonizes a 5-HT2 receptor
Zhou, Jian; Reidy, Mairead; O'Reilly, Ciaran; Jarikote, Dilip V.; Negi, Arvind; Samali, Afshin; Szegezdi, Eva; Murphy, Paul V. (American Chemical Society, 2015-03-16)A build-couple-pair strategy, including double-reductive amination macrocyclization, has been used to generate decorated macrocycles (eannaphanes) with an embedded triazole and monosaccharide. Biological screening led to ... -
Development of Mcl-1 inhibitors for cancer therapy
Negi, Arvind; Murphy, Paul V. (Elsevier, 2020-11-24)The myeloid leukemia cell differentiation protein (Mcl-1) is an anti-apoptotic protein of the B-cell lymphoma 2 (Bcl-2) family, which regulates cellular apoptosis. Mcl-1 expression plays a key role in survival of cancer ... -
Engineering a therapeutic lectin by uncoupling mitogenicity from antiviral activity
Swanson, Michael D.; Salmon, L.; Chugh, J.; Winter, H. C.; Meagher, J. L.; André, S.; Murphy, Paul V.; Oscarson, S.; Roy, R.; King, S.; Kaplan, M. H.; Goldstein, I. J.; Tarbet, E. B.; Hurst, B. L.; Smee, D. F.; de la Fuente, C.; Hoffmann, H. H.; Xue, Y.; Rice, C. M.; Schols, D.; Garcia, J. V.; Stuckey, J. A.; Gabius, H. J.; Al-Hashimi, H. M.; Markovitz, D. M.; Boudreaux, Daniel M. (Elsevier, 2015-10-22)A key effector route of the Sugar Code involves lectins that exert crucial regulatory controls by targeting distinct cellular glycans. We demonstrate that a¿¿single amino-acid substitution in a banana lectin, replacing ... -
Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity
O'Sullivan, Shane; Murphy, Paul V.; Gabius, Hans-Joachim; Sabine, Sabine (Elsevier, 2015-09-23)The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant ... -
Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation
Farrell, Mark P.; Doyle, Lisa M.; Murphy, Paul V. (Elsevier, 2018-05-26)Lewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-d-glucopyranosides was determined to determine how particular acyl protecting groups and ... -
Influence of protein (human galectin-3) design on aspects of lectin activity
Caballero, Gabriel Garcia; Beckwith, Donella; Shilova, Nadezhda, V.; Gabba, Adele; Kutzner, Tanja J.; Ludwig, Anna-Kristin; Manning, Joachim C.; Kaltner, Herbert; Sinowatz, Fred; Cudic, Mare; Bovin, Nicolai, V.; Murphy, Paul V.; Gabius, Hans-Joachim (Springer, 2020-04-25)The concept of biomedical significance of the functional pairing between tissue lectins and their glycoconjugate counterreceptors has reached the mainstream of research on the flow of biological information. A major challenge ... -
Inhibition of Burkholderia multivorans Adhesion to Lung Epithelial Cells by Bivalent Lactosides
Leyden, Rosaria; Murphy, Paul V. (MDPI, 2012-08-24)Burkholderia cepacia complex (Bcc) is an opportunistic pathogen in cystic fibrosis patients which is inherently resistant to antimicrobial agents. The mechanisms of attachment and pathogenesis of Bcc, a group of 17 species, ... -
Lectins: getting familiar with translators of the sugar code
Murphy, Paul V. (MDPI, 2015-01-22)The view on the significance of the presence of glycans in glycoconjugates is undergoing a paradigmatic change. Initially mostly considered to be rather inert and passive, the concept of the sugar code identifies glycans ... -
Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer
McDonagh, Anthony W.; Mahon, Mary F.; Murphy, Paul V. (American Chemical Society, 2016-01-22)The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid ... -
Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides
Doyle, Lisa M.; Meany, Fiach B.; Murphy, Paul V. (Elsevier, 2018-11-24)Pentopyranoside and 6-deoxyhexopyranosides, such as those from d-xylose, l-arabinose and l-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their ... -
Ligand design for somatostatin receptor isoforms 4 and 5
Negi, Arvind; Zhou, Jian; Sweeney, Sinclair; Murphy, Paul V. (Elsevier, 2018-11-17)The somatostatin receptor (SSTR) isoforms, SSTR-4 and SSTR-5 are targets in numerous disorders and diseases. Although there has been some success in achieving selective isoform inhibition, structure-based drug design and ...