Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre.

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dc.contributor.authorSchwarz, Maria
dc.contributor.authorMurphy, Edel J.
dc.contributor.authorFoley, Aoife M.
dc.contributor.authorWoods, David F.
dc.contributor.authorCastilla, Ignacio Abreu
dc.contributor.authorReen, F. Jerry
dc.contributor.authorCollins, Stuart G.
dc.contributor.authorO'Gara, Fergal
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderIrish Research Councilen
dc.contributor.funderThermo Fisher Scientificen
dc.contributor.funderGlaxoSmithKlineen
dc.contributor.funderEnterprise Irelanden
dc.contributor.funderHealth Research Boarden
dc.contributor.funderIrish Thoracic Societyen
dc.contributor.funderSeventh Framework Programmeen
dc.contributor.funderHorizon 2020en
dc.contributor.funderDepartment of Agriculture, Food and the Marine, Irelanden
dc.contributor.funderFood Institutional Research Measureen
dc.contributor.funderIrish Research Council for Science, Engineering and Technologyen
dc.contributor.funderCystic Fibrosis Foundationen
dc.date.accessioned2021-06-01T11:45:04Z
dc.date.available2021-06-01T11:45:04Z
dc.date.issued2020-10-23
dc.date.updated2021-05-31T10:17:25Z
dc.description.abstractThe marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme.en
dc.description.sponsorshipIrish Research Council, Thermo Fisher Scientific and GlaxoSmithKline (project number EPSPG/2016/41); Enterprise Ireland ((CF-2017-0757-P), (IP-2015-0390)); Health Research Board/Irish Thoracic Society ((MRCG-2018-16), (MRCG-2014-6)); The Health Research Board (ILP-POR-2019-004); European Commission (FP7-PEOPLE-2013-ITN, 607786; FP7-KBBE-2012-6, CP-TP-312184; FP7-KBBE-2012-6, 311975; OCEAN 2011-2, 287589; EU2020-634486-2015), Science Foundation Ireland (SSPC-3, 12/RC/2275; SSPC-2, 12/RC/2275; 13/TIDA/B2625; 12/TIDA/B2411; 12/TIDA/B2405; 14/TIDA/2438; 15/TIDA/2977; SFI09/RFP/BMT2350); Department of Agriculture and Food (FIRM 11/F009/MabS; FIRM 13/F/516); Irish Research Council for Science, Engineering and Technology (GOIPG/2014/647); Department of the Marine, Ireland (BEAU/BIOD/01), Cystic Fibrosis Foundation, USA (OG1710).en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationSchwarz, M., Murphy, E. J., Foley, A. M., Woods, D. F., Castilla, I. A., Reen, F. J., Collins, S. G., O'Gara, F. and Maguire, A. R. (2021) 'Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre', Organic & Biomolecular Chemistry, 19(1), pp. 188-198. doi: 10.1039/d0ob01848aen
dc.identifier.doi10.1039/d0ob01848aen
dc.identifier.endpage198en
dc.identifier.issn1477-0539
dc.identifier.issued1en
dc.identifier.journaltitleOrganic & Biomolecular Chemistryen
dc.identifier.startpage188en
dc.identifier.urihttps://hdl.handle.net/10468/11423
dc.identifier.volume19en
dc.language.isoenen
dc.publisherRoyal Society of Chemistryen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Infrastructure Programme/15/RI/3221/IE/Process Flow Spectroscopy (ProSpect); Advanced Reaction Understanding using Flow Nuclear Magnetic Resonance (NMR) and Infrared (IR) Spectroscopies, with On-Line Ultra-Performance Liquid Chromatography (UPLC) and Mass Spectrometry (MS)/en
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP3::PEOPLE/607786/EU/BluePharmTrain/BLUEPHARMTRAINen
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/312184/EU/Increasing Value and Flow in the Marine Biodiscovery Pipeline/PHARMASEAen
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/311975/EU/Marine Microorganisms: Cultivation Methods for Improving their Biotechnological Applications/MACUMBAen
dc.relation.projectinfo:eu-repo/grantAgreement/EC/FP7::SP1::KBBE/287589/EU/Marine Microbial Biodiversity, Bioinformatics and Biotechnology/MICRO B3en
dc.relation.projectinfo:eu-repo/grantAgreement/EC/H2020::IA/634486/EU/Industrial Applications of Marine Enzymes: Innovative screening and expression platforms to discover and use the functional protein diversity from the sea/INMAREen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/12/TIDA/B2411/IE/Development of small molecule therapeutics for medical intervention: anti-biofilm inhibitors for the medical device sector./en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/13/TIDA/B2625/IE/Small molecule inhibitors of HIF-1: a new class of anti-cancer therapeutics./en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/12/TIDA/B2405/IE/Optimised detection of key biomarkers of Pseudomonas aeruginosa towards a clinical application/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/14/TIDA/2438/IE/Next Generation Antibiotics: anti-biofilm, anti-pathogenic natural bioactives from marine microorganisms./en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/15/TIDA/2977/IE/Pre-clinical testing of novel fungal biofilm blockers for the medical device sector./en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Frontiers Programme (RFP)/09/RFP/BMT2350/IE/An investigation of the molecular interactions between statins and microbial pathogens and their combined impact on the human immune response./en
dc.relation.urihttps://pubs.rsc.org/en/content/articlelanding/2021/ob/d0ob01848a
dc.rights© The Royal Society of Chemistry 2021en
dc.subjectMarine microorganismen
dc.subjectBiotechnologyen
dc.subjectMedical therapeuticsen
dc.subjectMarine transaminaseen
dc.titleExploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre.en
dc.typeArticle (peer-reviewed)en
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