Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media
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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.
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 . DOI: 10.1002/cctc.201500190
© 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
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).
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