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dc.contributor.authorLo Re, D
dc.contributor.authorJones, L
dc.contributor.authorGiralt, E
dc.contributor.authorMurphy, P
dc.date.accessioned2020-01-22T13:10:55Z
dc.date.available2020-01-22T13:10:55Z
dc.date.issued2016-07-06
dc.identifier.citationJones, L., Lo Re, D., Giralt, E., & Murphy, P. (2016). Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose. Chemistry - An Asian Journal , 11(14), 2035- 2040. https://doi.org/10.1002/asia.201600736en
dc.identifier.issn1861-4728en
dc.identifier.pmid27304425
dc.identifier.doi10.1002/asia.201600736en
dc.identifier.urihttp://hdl.handle.net/2436/623010
dc.description.abstract© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The use of l-sorbose in the synthesis of functionalized cyclopentene derivatives was accomplished. These cyclopentene derivatives are related to those found in naturally occurring jatrophane frameworks and in other bioactive compounds. The formation of allyl α-l-sorbopyranoside was a key synthetic step. Regioselective introduction of protecting groups was followed by the hydrolysis of the allyl glycoside to furnish a fully protected acyclic l-sorbose derivative. This acyclic intermediate was subsequently used to give an orthogonally protected polyhydroxylated cyclopentene, which has potential for further synthesis of bioactive compounds. The protected cyclopentene itself showed a clear cytotoxic activity when tested against a panel of human cancer cell lines (HT29, LS174T, SW620, A549, and HeLa cells).en
dc.description.sponsorshipThis work was supported by Science Foundation Ireland (grant Nos. 07/IN.1/B966 and 11/TIDA/B2047). The research leading to these results also received funding from the People Programme (Marie Curie Actions) of the European Union's Seventh Framework Programme (FP7/2007–2013) under grant agreement number PIEF‐GA‐2011‐299042 and from the European Union's Seventh Framework Programme for research, technological development and demonstration under grant agreement no 600404 and from MINECO‐FEDER (Bio2013‐40716‐R). IRB Barcelona is the recipient of a Severo Ochoa Award of Excellence from MINECO (Government of Spain).en
dc.formatapplication/pdfen
dc.languageeng
dc.language.isoenen
dc.publisherWileyen
dc.relation.urlhttps://onlinelibrary.wiley.com/doi/full/10.1002/asia.201600736en
dc.subjectCarbohydratesen
dc.subjectchiral poolen
dc.subjectglycomimeticsen
dc.subjectMultidrug resistanceen
dc.subjectorthogonal protectionen
dc.titleSynthesis of an orthogonally protected polyhydroxylated cyclopentene from l-Sorboseen
dc.typeJournal articleen
dc.identifier.eissn1861-471X
dc.identifier.journalChemistry - An Asian Journalen
dc.date.updated2020-01-22T08:31:00Z
dc.contributor.institutionSchool of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland. daniele.lore@irbbarcelona.org.
pubs.place-of-publicationGermany
dc.date.accepted2016-05-15
rioxxterms.funderSFI Investigator Program/ IRCSET Embark Fellowship Programen
rioxxterms.identifier.project07/IN.1/B966, 11/TIDA/B2047, PIEF‐GA‐2011‐299042en
rioxxterms.versionAMen
rioxxterms.licenseref.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
rioxxterms.licenseref.startdate2020-01-22en
dc.source.volume11
dc.source.issue14
dc.source.beginpage2035
dc.source.endpage2040
dc.description.versionPublished version
refterms.dateFCD2020-01-22T13:10:01Z
refterms.versionFCDAM
refterms.dateFOA2020-01-22T13:10:56Z


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