Catalytic Modification of Dehydroalanine in Peptides and Proteins by Palladium-Mediated Cross-Coupling

Dowine de Bruijn, Gerard Roelfes

OnderzoeksoutputAcademicpeer review

13 Citaten (Scopus)
380 Downloads (Pure)

Samenvatting

Dehydroalanine (Dha) is a remarkably versatile non-canonical amino acid often found in antimicrobial peptides. Here we present the catalytic modification of Dha via a palladium mediated cross coupling reaction. 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 yields both the Heck product, in which the sp2-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.

Originele taal-2English
Pagina's (van-tot)12728-12733
TijdschriftChemistry
Volume24
Nummer van het tijdschrift48
Vroegere onlinedatum19-jun-2018
DOI's
StatusPublished - aug-2018

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