{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84239"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84239","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"I. Efforts Toward the Total Synthesis of (-)-Crambidine. II. Reactions of Azy(3-Me)-Containing Peptides With Thiols and Selenols","abstract":"An approach to (-)-crambidine, utilizing a key [4+2] annulation reaction between a thioimidate and an electron deficient vinyl carbodiimide, has been investigated. This approach has resulted in several advanced intermediates related to (-)-crambidine, but an efficient total synthesis of (-)-crambidine has not yet been completed. Additionally, an investigation into the base-promoted thiolysis and selenolysis of Azy(3-Me)-containing peptides has been performed. While thiols were found to have low reactivity with this class of electrophilic peptide residues, two S-linked glycopeptides were successfully synthesized. Benzeneselenol was found to be highly reactive with Azy(3-Me)-containing peptides, and a variety of synthetically useful selenopeptides have been generated.","abstract_html":"An approach to (-)-crambidine, utilizing a key [4+2] annulation reaction between a thioimidate and an electron deficient vinyl carbodiimide, has been investigated. This approach has resulted in several advanced intermediates related to (-)-crambidine, but an efficient total synthesis of (-)-crambidine has not yet been completed. Additionally, an investigation into the base-promoted thiolysis and selenolysis of Azy(3-Me)-containing peptides has been performed. While thiols were found to have low reactivity with this class of electrophilic peptide residues, two S-linked glycopeptides were successfully synthesized. Benzeneselenol was found to be highly reactive with Azy(3-Me)-containing peptides, and a variety of synthetically useful selenopeptides have been generated.","abstract_has_math":false,"creators":["Ide, Nathan D."],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Gin, David Y."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:13:36Z","date_published":"2015-09-25T22:13:36Z","updated_at":"2026-07-22T22:26:22Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI3242877"],"render_values":[{"text":"(MiAaPQ)AAI3242877","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84239","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gin, David Y."]},{"key":"dc:creator","label":"Author","values":["Ide, Nathan D."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:13:36Z","10000-01-01","2006"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84239","(MiAaPQ)AAI3242877"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["An approach to (-)-crambidine, utilizing a key [4+2] annulation reaction between a thioimidate and an electron deficient vinyl carbodiimide, has been investigated. 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