Side reactions in the SPPS of Cys-containing peptides

 
This item is provided by the institution :
University of Ioannina
Repository :
Repository of UOI Olympias
see the original item page
in the repository's web site and access all digital files if the item*
share



2013 (EN)
Side reactions in the SPPS of Cys-containing peptides (EN)

Stathopoulos, P. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Stathopoulos, P. (EN)

Alkylation of sensitive amino acids during synthesis of biologically important peptides is a common and well-documented problem in Fmoc-based strategy. Herein, we probed for the first time an unexpected S-alkylation of Cys-containing peptides that occur during the final TFA cleavage of peptides from the Wang solid support. Through a battery of approaches (NMR, UV and LC-MS) the formed by-product was assigned as the alkylation of the cysteine sulfydryl group by the p-hydroxyl benzyl group derived from the acidic Wang linker decomposition. Factors affecting this side reaction were monitored and a protocol that minimizes the presence of the by-product is reported. (EN)

Alkylation (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

Amino Acids (EN)

English

2013


Springer-Verlag (EN)



*Institutions are responsible for keeping their URLs functional (digital file, item page in repository site)