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dc.contributor.authorBaumann, Markus
dc.contributor.authorNome, Lina Marie
dc.contributor.authorZachariassen, Zack Georg
dc.contributor.authorKarlshøj, Stepfanie
dc.contributor.authorFossen, Torgils
dc.contributor.authorRosenkilde, Mette M.
dc.contributor.authorVåbenø, Jon
dc.contributor.authorHaug, Bengt Erik
dc.date.accessioned2018-02-09T09:17:20Z
dc.date.available2018-02-09T09:17:20Z
dc.date.issued2017-07
dc.PublishedBaumann M, Nome, Zachariassen ZG, Karlshøj, Fossen T, Rosenkilde MM, Våbenø J, Haug BE. Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron. 2017;73(27-28):3866-3877eng
dc.identifier.issn1464-5416en_US
dc.identifier.issn0040-4020en_US
dc.identifier.urihttps://hdl.handle.net/1956/17364
dc.descriptionUnder embargo until: 17.05.2019
dc.description.abstractWe here report the preparation of a new 2,6,8-trisubstituted bicyclic tripeptidomimetic scaffold through TFA-mediated cyclization of a linear precursor containing three side chains. The introduction of a triphenylmethyl-protected thiol into carboxylic acid containing building blocks through sulfa Michael additions onto α,β-unsaturated hexafluoroisopropyl esters is described. The stereoselectivity of the bicycle formation was found to be somewhat lower than that previously reported for analogous 3,6,8-trisubstituted scaffolds. Moreover, the configuration of the linear precursor directs the stereochemical outcome of the cyclization differently when the R1 side chain is positioned on C2 in the bicycles (present work) instead of C3 (previous work). Tripeptidomimetic compounds based on the new scaffold were synthesized and evaluated for antagonistic potency toward CXCR4, and one compound (45a) displayed similar activity to earlier reported 3,6,8-tripeptidomimetic bicycles.en_US
dc.language.isoengeng
dc.publisherElsevieren_US
dc.rightsAttribution CC BY-NC-NDeng
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/eng
dc.subjectTripeptidomimeticeng
dc.subjectScaffoldeng
dc.subjectCXCR4 antagonisteng
dc.titleSynthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonismen_US
dc.typePeer reviewed
dc.typeJournal article
dc.date.updated2018-01-30T08:50:39Z
dc.description.versionacceptedVersionen_US
dc.rights.holderCopyright 2017 Elsevieren_US
dc.identifier.doihttps://doi.org/10.1016/j.tet.2017.05.057
dc.identifier.cristin1485291
dc.source.journalTetrahedron


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