{"id":{"repo_id":"laurentian","oai_identifier":"oai:laurentian.scholaris.ca:10219/2699"},"canonical_url":"https://search.dev.ndltd.org/etd/laurentian/oai:laurentian.scholaris.ca:10219/2699","repository":{"repo_id":"laurentian","name":"Laurentian University","base_url":"https://laurentian.scholaris.ca/server/oai/request"},"display":{"title":"The synthesis of macrocyclic molecules related to telomestatin","abstract":"G-quadruplex DNA represents an attractive target for the development of anti-cancer therapeutic agents as it plays important roles in transcriptional regulation and the maintenance of telomeric length. Oxazole-containing macrocycles such as telomestatin are considered to be a promissing new class of G-quadruplex binding ligands. In this work, poly-oxazole building blocks were synthesized to prepare a tetraoxazole peptide macrocycle in good yield. The macrocycle was obtained by employing standard peptide coupling conditions using a convergent solution phase approach. The synthetic unit of the oxazole amino acid containing compound was prepared by cyclodehydration/oxidation of protected serine and phenylalanine. Two-cycle coupling of the unit gave a linear tetraoxazole amide. The final macrocyclization was accomplished by using O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and the product (45% yield) was characterized by 1H NMR. Finally, the Cu (II) coordination chemistry of the tetraoxazole macrocycle was investigated by spectrophotometric titration.","abstract_html":"G-quadruplex DNA represents an attractive target for the development of anti-cancer therapeutic agents as it plays important roles in transcriptional regulation and the maintenance of telomeric length. Oxazole-containing macrocycles such as telomestatin are considered to be a promissing new class of G-quadruplex binding ligands. In this work, poly-oxazole building blocks were synthesized to prepare a tetraoxazole peptide macrocycle in good yield. The macrocycle was obtained by employing standard peptide coupling conditions using a convergent solution phase approach. The synthetic unit of the oxazole amino acid containing compound was prepared by cyclodehydration/oxidation of protected serine and phenylalanine. Two-cycle coupling of the unit gave a linear tetraoxazole amide. The final macrocyclization was accomplished by using O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and the product (45% yield) was characterized by 1H NMR. Finally, the Cu (II) coordination chemistry of the tetraoxazole macrocycle was investigated by spectrophotometric titration.","abstract_has_math":false,"creators":["Aldarini, Wafa Saeed S."],"institution":"Laurentian University of Sudbury","degree_name":"Master of Science (MSc) in Chemical Sciences","degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017-01-13","date_published":"2017-01-13","updated_at":"2026-08-21T16:45:55Z","subjects":["G-quadruplexes","telomestatin","poly-oxazole macrocycles","macrocyclization","dinuclear copper (II) complex"],"languages":["en"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://laurentian.scholaris.ca/handle/10219/2699","outbound_label":"Repository record","outbound_source":"dc:identifier.uri"},"source_record":{"url":"https://laurentian.scholaris.ca/server/oai/request?verb=GetRecord&metadataPrefix=dim&identifier=oai%3Alaurentian.scholaris.ca%3A10219%2F2699","prefix":"dim"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Aldarini, Wafa Saeed S."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2017-02-09T14:31:54Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2017-02-09T14:31:54Z"]},{"key":"dc:date.issued","label":"Date","values":["2017-01-13"]},{"key":"dc:publisher","label":"Institution","values":["Laurentian University of Sudbury"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MSc) in Chemical Sciences"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["Laurentian University of Sudbury"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["G-quadruplexes","telomestatin","poly-oxazole macrocycles","macrocyclization","dinuclear copper (II) complex"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://laurentian.scholaris.ca/handle/10219/2699"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["G-quadruplex DNA represents an attractive target for the development of anti-cancer therapeutic agents as it plays important roles in transcriptional regulation and the maintenance of telomeric length. Oxazole-containing macrocycles such as telomestatin are considered to be a promissing new class of G-quadruplex binding ligands. In this work, poly-oxazole building blocks were synthesized to prepare a tetraoxazole peptide macrocycle in good yield. The macrocycle was obtained by employing standard peptide coupling conditions using a convergent solution phase approach. The synthetic unit of the oxazole amino acid containing compound was prepared by cyclodehydration/oxidation of protected serine and phenylalanine. Two-cycle coupling of the unit gave a linear tetraoxazole amide. The final macrocyclization was accomplished by using O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and the product (45% yield) was characterized by 1H NMR. Finally, the Cu (II) coordination chemistry of the tetraoxazole macrocycle was investigated by spectrophotometric titration."]},{"key":"dc:title","label":"Title","values":["The synthesis of macrocyclic molecules related to telomestatin"]}]}],"canonical_facts":{"dc:creator":["Aldarini, Wafa Saeed S."],"dc:date.accessioned":["2017-02-09T14:31:54Z"],"dc:date.available":["2017-02-09T14:31:54Z"],"dc:date.issued":["2017-01-13"],"dc:description.abstract":["G-quadruplex DNA represents an attractive target for the development of anti-cancer therapeutic agents as it plays important roles in transcriptional regulation and the maintenance of telomeric length. Oxazole-containing macrocycles such as telomestatin are considered to be a promissing new class of G-quadruplex binding ligands. In this work, poly-oxazole building blocks were synthesized to prepare a tetraoxazole peptide macrocycle in good yield. The macrocycle was obtained by employing standard peptide coupling conditions using a convergent solution phase approach. The synthetic unit of the oxazole amino acid containing compound was prepared by cyclodehydration/oxidation of protected serine and phenylalanine. Two-cycle coupling of the unit gave a linear tetraoxazole amide. The final macrocyclization was accomplished by using O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and the product (45% yield) was characterized by 1H NMR. Finally, the Cu (II) coordination chemistry of the tetraoxazole macrocycle was investigated by spectrophotometric titration."],"dc:identifier.uri":["https://laurentian.scholaris.ca/handle/10219/2699"],"dc:language.iso":["en"],"dc:publisher":["Laurentian University of Sudbury"],"dc:subject":["G-quadruplexes","telomestatin","poly-oxazole macrocycles","macrocyclization","dinuclear copper (II) complex"],"dc:title":["The synthesis of macrocyclic molecules related to telomestatin"],"dc:type":["Thesis"],"thesis:degree_name":["Master of Science (MSc) in Chemical Sciences"],"thesis:institution_name":["Laurentian University of Sudbury"]},"updated_at":"2026-08-21T16:45:55Z"}