Browsing by Author "Murphy, Paul V."
Now showing items 1-20 of 71
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(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 ... -
The anomerisation of glycosidic linkages
Farrell, Mark (2014-04-07)This thesis deals with the anomerisation of glycosidic linkages using TiCl4 and SnCl4. Methods involving the Lewis acid induced anomerisations of glycosides have been published over the past decade, however this methodology ... -
The anomerisation of glycosyl thiols and synthesis of multivalent GlcNAc and GalNAc glycoclusters
O'Sullivan, Shane (2015-04-29)There are several published procedures available for the synthesis of b-thiopyranoses such as gluco- or galacto-pyranoses. Given the ease with which one can access such b -thiopyranoses, the development of a reproducible ... -
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 ... -
Biological study of the angiogenesis inhibitor n-(8-(3-ethynylphenoxy)octyl-1-deoxynojirimycin
Zhao, Yunxue; Zhou, Ying; O’ Boyle, Kathy M.; Murphy, Paul V. (Wiley-Blackwell, 2010-06-01)The alpha-glucosidase inhibitors N-methyl-1-deoxynojirimycin (MDNJ) and castanospermine have been shown to inhibit angiogenesis. A hybrid of 1-deoxynojirimycin (DNJ) and an aryl-1,2,3-triazole, which inhibits both an ... -
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 ... -
Carbohydrates in the synthesis of macrocycles and glycoclusters
Fox, Karen A. (NUI Galway, 2019-01-28)This thesis deals with efforts to generate new bioactive organic compounds. The main focus has been on the use of carbohydrate building blocks for synthesis of both macrocyclic compounds and glycoclusters for biological ... -
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 ... -
Design and synthesis of novel constrained glycomimetics as inhibitors of galectins and galactosidases
Hever, Eoin (NUI Galway, 2023-10-10)Chapter 1 gives a brief introduction to carbohydrate structure, discussing factors influencing reactivity and conformation, such as the anomeric and exo-anomeric effect. Chapter 1 mentions methods of structural analysis ... -
Design, synthesis and evaluation of glycomimetics as galectin inhibitors
Dhara, Ashis (NUI Galway, 2024-03-11)Chapter-1: This chapter begins with a short review on carbohydrates and their structure and then summarises some highlights from the last two decades of research on developing carbohydrate-based drug candidates. Included ... -
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 ... -
Enzymes in the World of Computational Chemistry - Computational Studies on Structures, Dynamics, Mechanisms, and Specificity of Five Biologically Important Enzymes
Tian, Boxue (2012-10-30)The thesis demonstrates computational chemical methodology applied to some biologically important enzymes. Five enzymes have been studied, i.e. sortase A (SrtA), 2-Methyl-3-hydroxypyridine-5-carboxylic acid oxygenase ... -
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 ...