{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/67237"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/67237","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp","abstract":"The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.","abstract_html":"The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.","abstract_has_math":false,"creators":["Cheng, Michael Tung-Hai"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-13T20:11:00Z","date_published":"2014-12-13T20:11:00Z","updated_at":"2026-07-22T22:25:57Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8108462"],"render_values":[{"text":"(UMI)AAI8108462","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/67237","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Cheng, Michael Tung-Hai"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-13T20:11:00Z","10000-01-01","1980"]},{"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/2142/67237","(UMI)AAI8108462"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.","Attempts to synthesize polyandrocarpidines were unsuccessful; however, hexahydropolyandrocarpidines were synthesized. Therefore, various analogs of hexahydropolyandrocarpidine were synthesized to study the structure-activity relationship against Bacillus subtilis. It was determined that the compound with five methylene groups between the two nitrogens has the highest activity, that the cyclopropane ring is not required for activity but its presence enhances the antimicrobial activity, and that the chain length of the acyl part is important to the activity.","Made available in DSpace on 2014-12-13T20:11:00Z (GMT). No. of bitstreams: 1 8108462.pdf: 4396998 bytes, checksum: 3d4d0142b1a7d626309208b256ec2cfb (MD5) Previous issue date: 1980","Embargo set by: Seth Robbins for item 67415 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","170 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980."]},{"key":"dc:title","label":"Title","values":["Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp"]}]}],"canonical_facts":{"dc:creator":["Cheng, Michael Tung-Hai"],"dc:date":["2014-12-13T20:11:00Z","10000-01-01","1980"],"dc:description":["The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.","Attempts to synthesize polyandrocarpidines were unsuccessful; however, hexahydropolyandrocarpidines were synthesized. Therefore, various analogs of hexahydropolyandrocarpidine were synthesized to study the structure-activity relationship against Bacillus subtilis. It was determined that the compound with five methylene groups between the two nitrogens has the highest activity, that the cyclopropane ring is not required for activity but its presence enhances the antimicrobial activity, and that the chain length of the acyl part is important to the activity.","Made available in DSpace on 2014-12-13T20:11:00Z (GMT). No. of bitstreams: 1 8108462.pdf: 4396998 bytes, checksum: 3d4d0142b1a7d626309208b256ec2cfb (MD5) Previous issue date: 1980","Embargo set by: Seth Robbins for item 67415 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","170 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980."],"dc:identifier":["http://hdl.handle.net/2142/67237","(UMI)AAI8108462"],"dc:language":["eng"],"dc:subject":["Chemistry, Organic"],"dc:title":["Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:25:57Z"}