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http://hdl.handle.net/11375/9014
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DC Field | Value | Language |
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dc.contributor.advisor | Harrison, P.H.M. | en_US |
dc.contributor.author | Ahilan, Yasodha | en_US |
dc.date.accessioned | 2014-06-18T16:45:07Z | - |
dc.date.available | 2014-06-18T16:45:07Z | - |
dc.date.created | 2011-05-25 | en_US |
dc.date.issued | 2011 | en_US |
dc.identifier.other | opendissertations/4175 | en_US |
dc.identifier.other | 5193 | en_US |
dc.identifier.other | 2030023 | en_US |
dc.identifier.uri | http://hdl.handle.net/11375/9014 | - |
dc.description.abstract | <p>p.p1 {margin: 0.0px 0.0px 0.0px 0.0px; font: 11.0px Times; color: #454545} p.p2 {margin: 0.0px 0.0px 0.0px 0.0px; font: 11.0px Times; color: #2c2c2c} span.s1 {font: 9.0px Helvetica; color: #2c2c2c} span.s2 {font: 9.0px Helvetica; color: #5f5e5f} span.s3 {color: #2c2c2c} span.s4 {color: #5f5e5f} span.s5 {font: 8.5px Helvetica; color: #2c2c2c} span.s6 {color: #454545} span.s7 {font: 8.5px Helvetica} span.s8 {font: 8.5px Helvetica; color: #5f5e5f} span.s9 {color: #747474} span.s10 {color: #0a0a0a}</p> <p>β-Lactones are natural products containing a four-membered lactone ring and are</p> <p>potent inhibitors of various types of enzymes. The mechanism of β-Lactone ring formation</p> <p>was examined in vivo in order to identify the genes and proteins that effect cyclization.</p> <p>Incorporation experiments into ebelactone A, a polyketide-derived β-Lactone from</p> <p>Streptomyces ahuraviensis, were conducted. Doubly labelled sodium [1-</p> <p>¹³C,¹⁸0₂]propionate prepared from labelled cyanide and water was fed to the cultures of</p> <p>the organism to give labelled ebelactone A. ¹⁸0-induced isotopic shifts were observed for</p> <p>all oxygenated carbon atoms of the molecule indicating that these oxygen atoms are all</p> <p>derived from propionate. This result is consistent with formation of the β-Lactone ring by</p> <p>nucleophilic attack of the C-3 hydroxyl group of a polyketide precursor onto the C-l</p> <p>carbonyl carbon, and excludes other putative mechanisms for ring formation. Ebelactone</p> <p>A was chemically converted to its N-acetylcysteamine derivative (SNAC). Labelling</p> <p>experiments to test for conversion of this SNAC derivative to ebelactone A in vivo</p> <p>showed only a background chemical cyclization reaction.</p> | en_US |
dc.subject | Chemistry | en_US |
dc.subject | Chemistry | en_US |
dc.title | Biosynthesis of β-Lactones: Origin of the Oxygen Atoms and Mechanism of β-Lactone Ring Formation | en_US |
dc.type | thesis | en_US |
dc.contributor.department | Chemistry | en_US |
dc.description.degree | Master of Science (MS) | en_US |
Appears in Collections: | Open Access Dissertations and Theses |
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File | Size | Format | |
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fulltext.pdf | 27.26 MB | Adobe PDF | View/Open |
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