Premium
Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium‐Mediated Cross‐Coupling
Author(s) -
de Bruijn A. Dowine,
Roelfes Gerard
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802846
Subject(s) - dehydroalanine , chemistry , catalysis , palladium , nisin , coupling reaction , combinatorial chemistry , conjugated system , organic chemistry , lantibiotics , amino acid , biochemistry , antimicrobial , polymer
Dehydroalanine (Dha) is a remarkably versatile non‐canonical amino acid often found in antimicrobial peptides. Herein, we present the catalytic modification of Dha by a palladium‐mediated cross‐coupling reaction. By using Pd(EDTA)(OAc) 2 as water‐soluble catalyst, a variety of arylboronic acids was coupled to the dehydrated residues in proteins and peptides, such as Nisin. The cross‐coupling reaction gave both the Heck product, in which the sp 2 ‐hybridisation of the α‐carbon is retained, as well as the conjugated addition product. The reaction can be performed under mild aqueous conditions, which makes this method an attractive addition to the palette of bio‐orthogonal catalytic methods.