Files in this item
Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media
Item metadata
dc.contributor.author | Willemse, Tom | |
dc.contributor.author | Van Imp , Karolien | |
dc.contributor.author | Goss, Rebecca Jane Miriam | |
dc.contributor.author | Van Vlijmen, Herman W.T. | |
dc.contributor.author | Schepens, Wim | |
dc.contributor.author | Maes , Bert U.W. | |
dc.contributor.author | Ballet, Steven | |
dc.date.accessioned | 2015-08-10T15:10:01Z | |
dc.date.available | 2015-08-10T15:10:01Z | |
dc.date.issued | 2015-07-13 | |
dc.identifier.citation | Willemse , 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.201500190 | en |
dc.identifier.issn | 1867-3880 | |
dc.identifier.other | PURE: 197703287 | |
dc.identifier.other | PURE UUID: 1df783ca-505a-49b9-9234-3b086fa4ba27 | |
dc.identifier.other | Scopus: 84947127901 | |
dc.identifier.other | WOS: 000357962400009 | |
dc.identifier.uri | https://hdl.handle.net/10023/7170 | |
dc.description | The 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.abstract | The 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.iso | eng | |
dc.relation.ispartof | ChemCatChem | en |
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.201500190 | en |
dc.subject | Amino acids | en |
dc.subject | C-C coupling | en |
dc.subject | Palladium | en |
dc.subject | Peptides | en |
dc.subject | Homogenous catalysis | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media | en |
dc.type | Journal article | en |
dc.description.version | Postprint | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.1002/cctc.201500190 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2015-06-29 | |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/cctc.201500190/suppinfo | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.