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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.accessioned2018-04-03T07:13:55Z
dc.date.available2018-04-03T07:13:55Z
dc.date.issued2017-05-17
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.descriptionPublished version available in <a href=https://doi.org/10.1016/j.tet.2017.05.057> Tetrahedron 2017, 73 (27-28):3866-3877. </a>en_US
dc.identifier.citationBaumann, M., Nome, L. M., Zachariassen, Z. G., Karlshøj, S., Fossen, T., Rosenkilde, M. M. ... Haug, B. E. (2017). Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron. 73(27-28):3866-3877en_US
dc.identifier.cristinIDFRIDAID 1485291
dc.identifier.doi10.1016/j.tet.2017.05.057
dc.identifier.issn0040-4020
dc.identifier.issn1464-5416
dc.identifier.urihttps://hdl.handle.net/10037/12454
dc.language.isoengen_US
dc.publisherElsevieren_US
dc.relation.journalTetrahedron
dc.rights.accessRightsopenAccessen_US
dc.subjectTripeptidomimeticen_US
dc.subjectScaffolden_US
dc.subjectCXCR4 antagonisten_US
dc.subjectVDP::Medisinske Fag: 700::Basale medisinske, odontologiske og veterinærmedisinske fag: 710::Medisinsk biokjemi: 726en_US
dc.subjectVDP::Medical disciplines: 700::Basic medical, dental and veterinary science disciplines: 710::Medical biochemistry: 726en_US
dc.titleSynthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonismen_US
dc.typeJournal articleen_US
dc.typeTidsskriftartikkelen_US
dc.typePeer revieweden_US


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