Abstract
The synthesis of fluorine-containing endothiopeptide analogs by the reaction of perfluorinated dithiocarboxylic acids amides with esters of α-amino acids and dipeptides
Highlights
One of the main approaches to changing and increasing the biological activity of pharmacologically-important peptides is the incorporation of non-natural amino acids into their structures.[1]
We have proposed a new method for the synthesis of fluorinated endothiopeptide analogs containing the thiocarbonyl group and fluorine atoms in the main peptide chain, by the thioacylation reaction of corresponding α-amino acids and dipeptide esters with thioamides of perfluorinated dicarboxylic acids
As shown in the literature, introduction of a fluorine atom can be used as part of the strategy to increase the metabolic stability and lipophilicity of the peptide, which improves the absorption and transport of the agent to its biological target, thereby increasing the biological activity of pharmacologically-important peptides
Summary
One of the main approaches to changing and increasing the biological activity of pharmacologically-important peptides is the incorporation of non-natural amino acids into their structures.[1] Peptides containing fluorinated amino acid residues[2−4] and endothiopeptides, in which one of the peptidic bonds is replaced by a thiopeptidic bond,[5−6] have been widely studied over prior decades. In the design of pharmaceuticals, the introduction of a fluorine atom is used as part of strategy to increase the metabolic stability and lipophilicity of the peptide, which improved absorption and transport of the agent to its biological target.[20,21,22,23,24]. Endothiopeptides are prepared by the thionation reaction of the amide’s carbonyl group of the corresponding peptides.[25]
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