New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Medicina Molecular e Enfermidades Crónicasgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorGonzález Soengas, Raquel María
dc.contributor.authorLorca Carvajal, Marcos Antonio
dc.contributor.authorPampín Casal, María Begoña
dc.contributor.authorSánchez Pedregal, Víctor Manuel
dc.contributor.authorEstévez Cabanas, Ramón José
dc.contributor.authorEstévez Cabanas, Juan Carlos
dc.date.accessioned2020-11-02T12:41:56Z
dc.date.available2020-11-02T12:41:56Z
dc.date.issued2020
dc.description.abstractWe present the synthesis and structural study of a new peptidomimetic of morphiceptin, which can formally be considered as the result of the replacement of the central proline residue of this natural analgesic drug with a subunit of (1S,2R,3S,4S,5R)-2-amino-3,4,5-trihydroxycyclopentane-1-carboxylic acid, previously obtained from L-idose. An optimized synthesis of this trihydroxylated cispentacin derivative is also reported. Molecular docking calculations on the target receptor support a favorable role of the hydroxy substituents of the non-natural β-amino acid incorporated into the peptidomimeticgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from the Spanish Ministry of Science and Innovation (CTQ2009-08490), the Xunta de Galicia (Centro Singular de Investigación de Galicia, Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03; Project CN2011/037, project ED431C 2018/04 and Project GRC2014/040), the Principado de Asturias (FICYT IDI/2018/000181) and the European Union (European Regional Development Fund-ERDF). Partial financial support by Arcelor Mittal (R&D-Principado de Asturias; FUO-286-18). Conicyt research fellowship to ML (PFCHA/Doctorado Nacional/2018-21180427)gl
dc.identifier.citationSoengas, R.; Lorca, M.; Pampín, B.; Sánchez-Pedregal, V.M.; Estévez, R.J.; Estévez, J.C. New Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study. Molecules 2020, 25, 2574gl
dc.identifier.doi10.3390/molecules25112574
dc.identifier.essn1420-3049
dc.identifier.urihttp://hdl.handle.net/10347/23525
dc.language.isoenggl
dc.publisherMDPIgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN/Plan Nacional de I+D+i 2008-2011/CTQ2009-08490/ES
dc.relation.publisherversionhttps://doi.org/10.3390/molecules25112574gl
dc.rights© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)gl
dc.rightsAtribución 4.0 Internacional
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectMorphiceptingl
dc.subjectAlicyclic β-amino acidsgl
dc.subjectPeptidomimeticsgl
dc.subjectNitro sugarsgl
dc.subjectAnalgesicgl
dc.titleNew Morphiceptin Peptidomimetic Incorporating (1S,2R,3S,4S,5R)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Studygl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
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relation.isAuthorOfPublication19cdf079-dc1b-48b2-8bc9-c73d3601f141
relation.isAuthorOfPublication86b5b898-6642-4dd7-b2ee-117e2f4838ff
relation.isAuthorOfPublication.latestForDiscovery1d559411-d167-465b-ac9e-7c8661f5642d

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