Wydział Chemii

Mateusz Waliczek

Monika Kijewska

Piotr Stefanowicz

Zbigniew Szewczuk

2015

Amino Acids

47

1353-1365

10.1007/s00726-015-1967-4

Naukowa

Angielski

Artykuł

The aim of our research was to design an efficient method for the solid phase synthesis of carbonylated peptides. For this purpose, we designed and synthesized a fully protected derivative Fmoc-amino(2,5,5-trimetyhyl1,3-dioxolan-2-yl)acetic acid (Fmoc-Atda-OH) of a novel unnatural amino acid (Thr(O)-2-amino-3-oxo-butanoic acid). To obtain the mentioned derivative, two synthetic strategies were investigated using different reagents for carbonyl protection, ethane-1,2-diol and 2,2-dimethyl-propane-1,3-diol. The racemization of oxidized threonine was also analyzed and discussed. We successfully carried out the solid phase synthesis of peptides containing a Thr(O) moiety using Fmoc-Atda-OH according to the standard Fmoc strategy. The application of the designed building block allows the synthesis of peptides containing D,LThr(O) residue, which may be used as models of oxidatively modified peptides which occur in biological systems and are related to many diseases.

Oxidative stress, Oxidation, Carbonylation, Solid phase peptide synthesis, Carbonylated peptides, Posttranslational modification

CC-BY

http://dx.doi.org/10.1007/s00726-015-1967-4

http://link.springer.com