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.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71926 |
| Date | January 1984 |
| Creators | Lajoie, Gilles. |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 000214792, proquestno: AAINK66669, Theses scanned by UMI/ProQuest. |
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