{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/54266"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/54266","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"Stereochemical aspects of virginiamycin biosynthesis: biosynthesis of antibiotic A33853","abstract":"The biochemical pathways for the formation of the unusual amino acids found in virginiamycin M₁ and A33853 were investigated. Specifically tritiated and carbon 14 labeled serines were incorporated into virginiamycin M₁. (2S)-serine and (2S,3R)-[3-³H] serine were found to be precursors, thus giving evidence of stereochemical control in the formation of the oxazole moiety. This information allowed for postulation of a ring closure pathway. Stereochemical investigations were also carried out on the dehydroproline unit and it was shown that both (R) and (S) prolines were incorporated into the dehydroproline unit. (2S,3R)-[3-³H] proline was synthesized and upon incorporation lost the (3-³H) label as evidence of stereochemical control in the formation of the dehydroproline unit from a saturated precursor. The basic biosynthetic origins of A33853 were investigated by feeding of D-[U-¹⁴C] glucose, sodium [U-¹⁴C] acetate, (S)-[U-¹⁴C] lysine, (S)-[U-¹⁴C] aspartic acid, [carboxyl-¹⁴C] anthranilic acid, and (S)-[5-³H] tryptophan. D-[U-¹⁴C]. Glucose and (S)-[U-¹⁴C] lysine appeared to be the main precursors. ¹³C¹⁵N lysine was synthesized and used to examine the ring closure of the 3-hydroxypicolinic amide ring in virginiamycin S₁.","abstract_html":"The biochemical pathways for the formation of the unusual amino acids found in virginiamycin M₁ and A33853 were investigated. Specifically tritiated and carbon 14 labeled serines were incorporated into virginiamycin M₁. (2S)-serine and (2S,3R)-[3-³H] serine were found to be precursors, thus giving evidence of stereochemical control in the formation of the oxazole moiety. This information allowed for postulation of a ring closure pathway. Stereochemical investigations were also carried out on the dehydroproline unit and it was shown that both (R) and (S) prolines were incorporated into the dehydroproline unit. (2S,3R)-[3-³H] proline was synthesized and upon incorporation lost the (3-³H) label as evidence of stereochemical control in the formation of the dehydroproline unit from a saturated precursor. The basic biosynthetic origins of A33853 were investigated by feeding of D-[U-¹⁴C] glucose, sodium [U-¹⁴C] acetate, (S)-[U-¹⁴C] lysine, (S)-[U-¹⁴C] aspartic acid, [carboxyl-¹⁴C] anthranilic acid, and (S)-[5-³H] tryptophan. D-[U-¹⁴C]. Glucose and (S)-[U-¹⁴C] lysine appeared to be the main precursors. ¹³C¹⁵N lysine was synthesized and used to examine the ring closure of the 3-hydroxypicolinic amide ring in virginiamycin S₁.","abstract_has_math":false,"creators":["Purvis, Michael Bernard"],"institution":"Virginia Polytechnic Institute and State University","degree_name":"Ph. D.","degree_level":"doctoral","degree_discipline":"Chemistry","degree_department":"Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":["Kingston, David G. I."],"committee_members":["Bell, Harold M.","White, Robert H.","Dorn, Harry C.","Lewis, N.G."],"year":1989,"date_issued":"1989","date_published":"1989","updated_at":"2026-07-22T22:20:12Z","subjects":[],"languages":["en_US"],"rights":["In Copyright"],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/10919/54266","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.committeechair","label":"Committee Chair","values":["Kingston, David G. 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(2S)-serine and (2S,3R)-[3-³H] serine were found to be precursors, thus giving evidence of stereochemical control in the formation of the oxazole moiety. This information allowed for postulation of a ring closure pathway. Stereochemical investigations were also carried out on the dehydroproline unit and it was shown that both (R) and (S) prolines were incorporated into the dehydroproline unit. (2S,3R)-[3-³H] proline was synthesized and upon incorporation lost the (3-³H) label as evidence of stereochemical control in the formation of the dehydroproline unit from a saturated precursor. The basic biosynthetic origins of A33853 were investigated by feeding of D-[U-¹⁴C] glucose, sodium [U-¹⁴C] acetate, (S)-[U-¹⁴C] lysine, (S)-[U-¹⁴C] aspartic acid, [carboxyl-¹⁴C] anthranilic acid, and (S)-[5-³H] tryptophan. D-[U-¹⁴C]. Glucose and (S)-[U-¹⁴C] lysine appeared to be the main precursors. ¹³C¹⁵N lysine was synthesized and used to examine the ring closure of the 3-hydroxypicolinic amide ring in virginiamycin S₁."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph. D."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Stereochemical aspects of virginiamycin biosynthesis: biosynthesis of antibiotic A33853"]}]}],"canonical_facts":{"dc:contributor.committeechair":["Kingston, David G. I."],"dc:contributor.committeemember":["Bell, Harold M.","White, Robert H.","Dorn, Harry C.","Lewis, N.G."],"dc:contributor.department":["Chemistry"],"dc:creator":["Purvis, Michael Bernard"],"dc:date.accessioned":["2015-07-09T20:43:28Z"],"dc:date.available":["2015-07-09T20:43:28Z"],"dc:date.issued":["1989"],"dc:description.abstract":["The biochemical pathways for the formation of the unusual amino acids found in virginiamycin M₁ and A33853 were investigated. Specifically tritiated and carbon 14 labeled serines were incorporated into virginiamycin M₁. (2S)-serine and (2S,3R)-[3-³H] serine were found to be precursors, thus giving evidence of stereochemical control in the formation of the oxazole moiety. This information allowed for postulation of a ring closure pathway. Stereochemical investigations were also carried out on the dehydroproline unit and it was shown that both (R) and (S) prolines were incorporated into the dehydroproline unit. (2S,3R)-[3-³H] proline was synthesized and upon incorporation lost the (3-³H) label as evidence of stereochemical control in the formation of the dehydroproline unit from a saturated precursor. The basic biosynthetic origins of A33853 were investigated by feeding of D-[U-¹⁴C] glucose, sodium [U-¹⁴C] acetate, (S)-[U-¹⁴C] lysine, (S)-[U-¹⁴C] aspartic acid, [carboxyl-¹⁴C] anthranilic acid, and (S)-[5-³H] tryptophan. D-[U-¹⁴C]. Glucose and (S)-[U-¹⁴C] lysine appeared to be the main precursors. ¹³C¹⁵N lysine was synthesized and used to examine the ring closure of the 3-hydroxypicolinic amide ring in virginiamycin S₁."],"dc:description.degree":["Ph. D."],"dc:format.mimetype":["application/pdf"],"dc:identifier.uri":["http://hdl.handle.net/10919/54266"],"dc:language.iso":["en_US"],"dc:publisher":["Virginia Polytechnic Institute and State University"],"dc:rights":["In Copyright"],"dc:rights.uri":["http://rightsstatements.org/vocab/InC/1.0/"],"dc:title":["Stereochemical aspects of virginiamycin biosynthesis: biosynthesis of antibiotic A33853"],"dc:type":["Dissertation"],"dc:type.dcmitype":["Text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["doctoral"],"thesis:degree_name":["Ph. D."],"thesis:institution_name":["Virginia Polytechnic Institute and State University"]},"updated_at":"2026-07-22T22:20:12Z"}