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dc.contributor.authorWillemse, Tom
dc.contributor.authorVan Imp , Karolien
dc.contributor.authorGoss, Rebecca Jane Miriam
dc.contributor.authorVan Vlijmen, Herman W.T.
dc.contributor.authorSchepens, Wim
dc.contributor.authorMaes , Bert U.W.
dc.contributor.authorBallet, Steven
dc.date.accessioned2015-08-10T15:10:01Z
dc.date.available2015-08-10T15:10:01Z
dc.date.issued2015-07-13
dc.identifier.citationWillemse , T , Van Imp , K , Goss , R J M , Van Vlijmen , H W T , Schepens , W , Maes , B U W & Ballet , S 2015 , ' Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media ' , ChemCatChem , vol. 7 , no. 14 , pp. 2055-2070 . https://doi.org/10.1002/cctc.201500190en
dc.identifier.issn1867-3880
dc.identifier.otherPURE: 197703287
dc.identifier.otherPURE UUID: 1df783ca-505a-49b9-9234-3b086fa4ba27
dc.identifier.otherScopus: 84947127901
dc.identifier.otherWOS: 000357962400009
dc.identifier.urihttp://hdl.handle.net/10023/7170
dc.descriptionThe authors gratefully acknowledge the IWT Flanders and Janssen Pharmaceutica for financial support of T.W. This work is supported by the Scientific Research Network (WOG) “Sustainable chemistry for the synthesis of fine chemicals” of the Research Foundation - Flanders (FWO).en
dc.description.abstractThe Suzuki-Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with much potential utility for medicinal chemistry and chemical biology. Here we report the modification of unprotected and Boc-protected aromatic amino acids and dipeptides in aqueous media, enabling heteroarylation and vinylation. We systematically investigate the impact of the peptide backbone and adjacent amino acid residues upon the reaction. Our studies reveal that whilst asparagine and histidine hinder the reaction, by utilising dppf, a ferrocene-based bidentate phosphine ligand, cross-coupling of halophenylalanine or halotryptophan adjacent to such a residue could be enabled. Our studies reveal dppf to have good compatibility with all unprotected, proteinogenic amino acid side chains.
dc.language.isoeng
dc.relation.ispartofChemCatChemen
dc.rights© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Willemse, T., Van Imp, K., Goss, R. J. M., Van Vlijmen, H. W. T., Schepens, W., Maes, B. U. W. and Ballet, S. (2015), Suzuki–Miyaura Diversification of Amino Acids and Dipeptides in Aqueous Media. ChemCatChem, 7: 2055–2070, which has been published in final form at http://dx.doi.org/10.1002/cctc.201500190en
dc.subjectAmino acidsen
dc.subjectC-C couplingen
dc.subjectPalladiumen
dc.subjectPeptidesen
dc.subjectHomogenous catalysisen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleSuzuki-Miyaura diversification of amino acids and dipeptides in aqueous mediaen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1002/cctc.201500190
dc.description.statusPeer revieweden
dc.date.embargoedUntil2015-06-29
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/cctc.201500190/suppinfoen


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