Publication
Title
Suzuki-Miyaura diversification of amino acids and dipeptides in aqueous media
Author
Abstract
The Suzuki--Miyaura derivatisation of free amino acids, peptides and proteins is an attractive area with considerable 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 although 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.
Language
English
Source (journal)
ChemCatChem. - -
Publication
2015
ISSN
1867-3880
1867-3899 [online]
Volume/pages
7:14(2015), p. 2055-2070
ISI
000357962400009
Full text (Publisher's DOI)
UAntwerpen
Faculty/Department
Research group
Project info
Peptide diversification: Pd-catalyzed derivatization of lead compounds in aqueous medium.
Durable chemical processes for the synthesis of fine chemicals.
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 28.07.2015
Last edited 03.12.2017
To cite this reference