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Stereochemical aspects of virginiamycin biosynthesis: biosynthesis of antibiotic A33853

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dc.contributor.authorPurvis, Michael Bernarden
dc.contributor.committeechairKingston, David G. I.en
dc.contributor.committeememberBell, Harold M.en
dc.contributor.committeememberWhite, Robert H.en
dc.contributor.committeememberDorn, Harry C.en
dc.contributor.committeememberLewis, N.G.en
dc.contributor.departmentChemistryen
dc.date.accessioned2015-07-09T20:43:28Zen
dc.date.available2015-07-09T20:43:28Zen
dc.date.issued1989en
dc.description.abstractThe 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.en
dc.description.degreePh. D.en
dc.format.extentxvii, 200 leavesen
dc.format.mimetypeapplication/pdfen
dc.identifier.urihttp://hdl.handle.net/10919/54266en
dc.language.isoen_USen
dc.publisherVirginia Polytechnic Institute and State Universityen
dc.relation.isformatofOCLC# 20139789en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1989.P878en
dc.subject.lcshAntibiotics -- Synthesisen
dc.titleStereochemical aspects of virginiamycin biosynthesis: biosynthesis of antibiotic A33853en
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

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