{"id":{"repo_id":"lsu-thes","oai_identifier":"oai:repository.lsu.edu:gradschool_dissertations-2145"},"canonical_url":"https://search.dev.ndltd.org/etd/lsu-thes/oai:repository.lsu.edu:gradschool_dissertations-2145","repository":{"repo_id":"lsu-thes","name":"Lousiana State University","base_url":"https://repository.lsu.edu/do/oai/"},"display":{"title":"Design and synthesis of handles for solid-phase peptide synthesis and convergent peptide synthesis","abstract":"The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N<sup>&#945;</sup>-amino protection has created a need for compatible anchoring linkages and handles. In an effort to develop mild new methods for use in solid-phase peptide synthesis (SPPS), a new ferrocene containing linker or “handle”, the 1’1-ferrocenyl carboxaldehyde handle was designed, synthesized, characterized and tested. This linker is analogous to those commercially available and developed by Barany. The ferrocenyl amine linker(FAL) releases C-terminal peptide amides upon acidolysis. Since the FAL handle is acid labile it is compatible with Fmoc and N<sup>&#945;</sup>-dithiasuccinoyl (Dts) based chemistries, but not N<sup>&#945;</sup>-tert-butyloxycarbonyl (Boc) based chemistries. The solid-phase linkage was investigated based on the stability of the ferrocenium ion. The stability of this ion is greater than that of the benzyl cations that are used in the handles developed previously.","abstract_html":"The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N&lt;sup&gt;&amp;#945;&lt;/sup&gt;-amino protection has created a need for compatible anchoring linkages and handles. In an effort to develop mild new methods for use in solid-phase peptide synthesis (SPPS), a new ferrocene containing linker or “handle”, the 1’1-ferrocenyl carboxaldehyde handle was designed, synthesized, characterized and tested. This linker is analogous to those commercially available and developed by Barany. The ferrocenyl amine linker(FAL) releases C-terminal peptide amides upon acidolysis. Since the FAL handle is acid labile it is compatible with Fmoc and N&lt;sup&gt;&amp;#945;&lt;/sup&gt;-dithiasuccinoyl (Dts) based chemistries, but not N&lt;sup&gt;&amp;#945;&lt;/sup&gt;-tert-butyloxycarbonyl (Boc) based chemistries. The solid-phase linkage was investigated based on the stability of the ferrocenium ion. The stability of this ion is greater than that of the benzyl cations that are used in the handles developed previously.","abstract_has_math":false,"creators":["Giraldes, Jose"],"institution":"Chemistry","degree_name":"Doctor of Philosophy (PhD)","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2003,"date_issued":"2003-01-01T08:00:00Z","date_published":"2003-01-01T08:00:00Z","updated_at":"2026-07-24T02:59:03Z","subjects":["ferrocenylamine","ferrocene","ferrocenyl","ligation","peptide"],"languages":[],"rights":["unrestricted","Release the entire work immediately for access worldwide."],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["etd-0407103-115838","https://repository.lsu.edu/gradschool_dissertations/1146"],"render_values":[{"text":"etd-0407103-115838","href":null,"code":true},{"text":"https://repository.lsu.edu/gradschool_dissertations/1146","href":"https://repository.lsu.edu/gradschool_dissertations/1146","code":true}]}]},"links":{"outbound_url":"https://doi.org/10.31390/gradschool_dissertations.1146","outbound_label":"DOI","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Giraldes, Jose"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2003-04-01"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-05-12T23:11:10Z"]},{"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":["Doctor of Philosophy (PhD)"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["Chemistry"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["ferrocenylamine","ferrocene","ferrocenyl","ligation","peptide"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["unrestricted","Release the entire work immediately for access worldwide."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["etd-0407103-115838","10.31390/gradschool_dissertations.1146","https://repository.lsu.edu/gradschool_dissertations/1146"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N<sup>&#945;</sup>-amino protection has created a need for compatible anchoring linkages and handles. In an effort to develop mild new methods for use in solid-phase peptide synthesis (SPPS), a new ferrocene containing linker or “handle”, the 1’1-ferrocenyl carboxaldehyde handle was designed, synthesized, characterized and tested. This linker is analogous to those commercially available and developed by Barany. The ferrocenyl amine linker(FAL) releases C-terminal peptide amides upon acidolysis. Since the FAL handle is acid labile it is compatible with Fmoc and N<sup>&#945;</sup>-dithiasuccinoyl (Dts) based chemistries, but not N<sup>&#945;</sup>-tert-butyloxycarbonyl (Boc) based chemistries. The solid-phase linkage was investigated based on the stability of the ferrocenium ion. The stability of this ion is greater than that of the benzyl cations that are used in the handles developed previously."]},{"key":"dc:title","label":"Title","values":["Design and synthesis of handles for solid-phase peptide synthesis and convergent peptide synthesis"]}]}],"canonical_facts":{"dc:creator":["Giraldes, Jose"],"dc:date":["2003-04-01"],"dc:date.available":["2022-05-12T23:11:10Z"],"dc:description.abstract":["The recent popularity of methods for solid-phase peptide synthesis that use the 9-fluorenylmethyloxycarbonyl (Fmoc) group for N<sup>&#945;</sup>-amino protection has created a need for compatible anchoring linkages and handles. In an effort to develop mild new methods for use in solid-phase peptide synthesis (SPPS), a new ferrocene containing linker or “handle”, the 1’1-ferrocenyl carboxaldehyde handle was designed, synthesized, characterized and tested. This linker is analogous to those commercially available and developed by Barany. The ferrocenyl amine linker(FAL) releases C-terminal peptide amides upon acidolysis. Since the FAL handle is acid labile it is compatible with Fmoc and N<sup>&#945;</sup>-dithiasuccinoyl (Dts) based chemistries, but not N<sup>&#945;</sup>-tert-butyloxycarbonyl (Boc) based chemistries. The solid-phase linkage was investigated based on the stability of the ferrocenium ion. The stability of this ion is greater than that of the benzyl cations that are used in the handles developed previously."],"dc:identifier":["etd-0407103-115838","10.31390/gradschool_dissertations.1146","https://repository.lsu.edu/gradschool_dissertations/1146"],"dc:rights":["unrestricted","Release the entire work immediately for access worldwide."],"dc:subject":["ferrocenylamine","ferrocene","ferrocenyl","ligation","peptide"],"dc:title":["Design and synthesis of handles for solid-phase peptide synthesis and convergent peptide synthesis"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy (PhD)"],"thesis:institution_name":["Chemistry"]},"updated_at":"2026-07-24T02:59:03Z"}