McGarrigle, Eoghan M.

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McGarrigle, Eoghan M.
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McGarrigle, Eoghan M.

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  • Publication
    Synthesis of Isothiocineole and Application in Multi-gram Scale Sulfur Ylide-mediated Asymmetric Epoxidation and Aziridination
    (Thieme, 2018-07-19)
    Fearraigh, Martin P. 
    ;
    Matlock, Johnathan V. 
    ;
    Illa, Ona 
    ;
    McGarrigle, Eoghan M. 
    ;
    Aggarwal, Varinder K. 
    The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.
      292Scopus© Citations 7
  • Publication
    Non-photopic and photopic visual cycles differentially regulate immediate, early and late-phases of cone photoreceptor-mediated vision
    (American Society for Biochemistry and Molecular Biology, 2020-05-08)
    Ward, Rebecca 
    ;
    Kaylor, Joanna J. 
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    Cobice, Diego F. 
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    Pepe, Dionysia Varvara 
    ;
    McGarrigle, Eoghan M. 
    ;
    Kennedy, Breandán 
    ;
    et al. 
    Cone photoreceptors in the retina enable vision over a wide range of light intensities. However, the processes enabling cone vision in bright light (i.e. photopic vision) are not adequately understood. Chromophore regeneration of cone photopigments may require the retinal pigment epithelium (RPE) and/or retinal Müller glia. In the RPE, isomerization of all-trans-retinyl esters (atRE) to 11-cis-retinol (11cROL) is mediated by the retinoid isomerohydrolase Rpe65. A putative alternative retinoid isomerase, dihydroceramide desaturase-1 (DES1), is expressed in RPE and Müller cells. The retinol-isomerase activities of Rpe65 and Des1 are inhibited by emixustat and fenretinide, respectively. Here, we tested the effects of these visual cycle inhibitors on immediate, early and late phases of cone photopic vision. In zebrafish larvae raised under cyclic light conditions, fenretinide impaired late cone photopic vision, whereas emixustat-treated zebrafish unexpectedly had normal vision. In contrast, emixustat-treated larvae raised under extensive dark-adaption displayed significantly attenuated immediate photopic vision concomitant with significantly reduced 11-cis-retinaldehyde (11cRAL). Following 30 minutes of light, early photopic vision recovered, despite 11cRAL levels remaining significantly reduced. Defects in immediate cone photopic vision were rescued in emixustat- or fenretinide-treated larvae following exogenous 9-cis-retinaldehyde (9cRAL) supplementation. Genetic knockout of Des1 (degs1) or retinaldehyde-binding protein 1b (rlbp1b) did not eliminate photopic vision in zebrafish. Our findings define molecular and temporal requirements of the non-photopic or photopic visual cycles for mediating vision in bright light.
      211Scopus© Citations 12
  • Publication
    Benzylation Reactions in DMF Lead to an Impurity Which Acts as an Organocatalyst Poison in Thiourea-Catalyzed Glycosylations
    (ACS, 2016-10-25)
    Colgan, Avene C. 
    ;
    Müller-Bunz, Helge 
    ;
    McGarrigle, Eoghan M. 
    The benzylation of alcohols with the commonly used combination of benzyl bromide and sodium hydride in DMF can lead to the formation of an amine side product, N,N′-dimethyl-1-phenyl-1-(o-tolyl)methanamine. This amine coeluted with benzylated galactal during column chromatography and was found to be a catalyst poison in thiourea-catalyzed glycosylations of galactals. It may also be problematic for other base-sensitive reactions involving benzylated substrates. Solutions to this problem are described.
      412Scopus© Citations 12