A methodology for the chain extension of N-protected amino acid beta-keto esters to gamma-keto esters utilizing a zinc carbenoid was developed. The reaction was used on amino acids containing various protective groups and a variety of side chain functionality. This method was used in the incorporation of ketomethylene isosteric amino acid replacements within amino acid sequences. The usefulness of the method on molecules supported by a solid phase was explored.
","abstract_html":"<p>A methodology for the chain extension of N-protected amino acid beta-keto esters to gamma-keto esters utilizing a zinc carbenoid was developed. The reaction was used on amino acids containing various protective groups and a variety of side chain functionality. This method was used in the incorporation of ketomethylene isosteric amino acid replacements within amino acid sequences. The usefulness of the method on molecules supported by a solid phase was explored.</p>","abstract_has_math":false,"creators":["Theberge, Cory Robert"],"institution":null,"degree_name":"Doctor of Philosophy","degree_level":"Dissertation","degree_discipline":null,"degree_department":null,"school":null,"contributors":["Charles K Zercher"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2002,"date_issued":"2002-01-01T08:00:00Z","date_published":"2002-01-01T08:00:00Z","updated_at":"2026-07-24T05:21:54Z","subjects":["Chemistry","Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://scholars.unh.edu/dissertation/82","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Charles K Zercher"]},{"key":"dc:creator","label":"Author","values":["Theberge, Cory Robert"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Doctor of Philosophy"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry","Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholars.unh.edu/dissertation/82"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["A methodology for the chain extension of N-protected amino acid beta-keto esters to gamma-keto esters utilizing a zinc carbenoid was developed. The reaction was used on amino acids containing various protective groups and a variety of side chain functionality. This method was used in the incorporation of ketomethylene isosteric amino acid replacements within amino acid sequences. The usefulness of the method on molecules supported by a solid phase was explored.
"]},{"key":"dc:title","label":"Title","values":["Ketomethylene isosteric amide bond replacements via the zinc -mediated chain extension of N -protected amino acids"]}]}],"canonical_facts":{"dc:contributor":["Charles K Zercher"],"dc:creator":["Theberge, Cory Robert"],"dc:description.abstract":["A methodology for the chain extension of N-protected amino acid beta-keto esters to gamma-keto esters utilizing a zinc carbenoid was developed. The reaction was used on amino acids containing various protective groups and a variety of side chain functionality. This method was used in the incorporation of ketomethylene isosteric amino acid replacements within amino acid sequences. The usefulness of the method on molecules supported by a solid phase was explored.
"],"dc:identifier":["https://scholars.unh.edu/dissertation/82"],"dc:subject":["Chemistry","Organic"],"dc:title":["Ketomethylene isosteric amide bond replacements via the zinc -mediated chain extension of N -protected amino acids"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Doctor of Philosophy"]},"updated_at":"2026-07-24T05:21:54Z"}