Thiocarbonyl analogues of amino acids and peptides : synthesis and biological properties

• Main Author: Lajoie, Gilles.
• Format: Others
• Language: en
• Published: McGill University 1984
• Subjects: Thiocarbonyl compounds.; Peptides.; Amino acids.
• Online Access: http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=71926

New thionation experimental conditions and new reagents for the synthesis of thioamide analogues of protected amino acids and peptides are presented. The interaction of thiocarbonyl analogues of model substrates of (alpha)-chymotrypsin and leucine aminopeptidase were also studied. Optically active dithioester derivatives of protected amino acids were prepared and used as thioacylating agents. === The synthesis of four thioamide-containing analogues of the chemotactic tripeptide f-Met-Leu-Phe was accomplished. The conformational properties of these novel analogues were studied by ('1)H and ('13)C NMR spectroscopy. Their biological activity was also evaluated in vitro and the results interpreted in terms of their molecular properties. === The regioselectivity of the new thionation methodology allowed for the rapid and efficient synthesis of the four possible monothioamide positional isomers of {Leu('5)}-enkephalin. Their biological activity was studied both in vitro and in vivo. === Amidoxime and amidrazide analogues of the peptidic bond were also obtained using thioamides as intermediates.