The synthesis of an analog of Leucine enkephalin bearing a thioamide linkage in position 3 was accomplished. Attempts to couple thiodipeptides to amines by the means of activating their free carboxyl function was showed to give substituted thiazolones which were not found suitable for the synthesis of thiopeptides. Many attempts to generate new thioacylating aminoacid derivatives are described. Three types of variously substituted thioacylbenzoxazolinones were efficiently synthesized and showed good thioacylating properties. At least one of them fulfill all the requirements for performing thiopeptide synthesis on a routine basis when applied to chiral aminoacid residues.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.71997 |
| Date | January 1985 |
| Creators | Lépine, François. |
| 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: 000218926, proquestno: AAINL20860, Theses scanned by UMI/ProQuest. |
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