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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.

SUBMITTER: Waliczek M

PROVIDER: S-EPMC4458268 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Site-selective solid phase synthesis of carbonylated peptides.

Waliczek Mateusz M Kijewska Monika M Stefanowicz Piotr P Szewczuk Zbigniew Z

Amino acids 20150327 7

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-propan ...[more]

PMID: 25813939

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