title: Site-selective solid phase synthesis of carbonylated peptides.
abstract: 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-trimetyhyl-1,3-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,L-Thr(O) residue, which may be used as models of oxidatively modified peptides which occur in biological systems and are related to many diseases.
authors: Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors: Mateusz
authors: M
authors: Waliczek
authors: Monika
authors: M
authors: Kijewska
authors: Piotr
authors: P
authors: Stefanowicz
authors: Zbigniew
authors: Z
authors: Szewczuk
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry; D050050:Protein Carbonylation; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D009842:Oligopeptides; D020005:Propanols