Repository logo
 

Precursor-Directed Biosynthesis of Novel Jadomycins and Expansion of the Jadomycin Library

dc.contributor.authorDupuis, Stephanie
dc.contributor.copyright-releaseNot Applicableen_US
dc.contributor.degreeMaster of Scienceen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.contributor.ethics-approvalNot Applicableen_US
dc.contributor.external-examinerDr. Frances Cozensen_US
dc.contributor.graduate-coordinatorDr. Mark Stradiottoen_US
dc.contributor.manuscriptsYesen_US
dc.contributor.thesis-readerDr. Jean Burnellen_US
dc.contributor.thesis-readerDr. Ray Syvitskien_US
dc.contributor.thesis-supervisorDr. David Jakemanen_US
dc.date.accessioned2010-09-09T15:13:15Z
dc.date.available2010-09-09T15:13:15Z
dc.date.defence2010-08-13
dc.date.issued2010-09-09
dc.description.abstractJadomycins are secondary metabolites produced by Streptomyces venezuelae ISP5230 VS1099 in response to conditions of stress such as heat or ethanol shock. They have been shown to exhibit antibiotic and anticancer activity. Unique structural features of the jadomycins include a rare 2,6-dideoxysugar, L-digitoxose, and an oxazolone ring with an amino acid component. Previous studies have revealed that jadomycin derivatives can be produced by altering the amino acid in S. venezuelae ISP5230 VS1099 culture media which becomes incorporated into the oxazolone ring. One jadomycin from a proteogenic amino acid and three new jadomycins from non-proteogenic amino acids have been successfully produced on a large scale (4 mg/L to 12 mg/L, 2 L) and characterized using mass spectrometry, infrared spectroscopy, UV-visible spectroscopy, and nuclear magnetic resonance spectroscopy. One of these contains a terminal alkyne functionality and has been used in cycloaddition reactions with various azides to produce a library of triazole-containing jadomycins.en_US
dc.identifier.urihttp://hdl.handle.net/10222/13053
dc.language.isoenen_US
dc.subjectjadomycinen_US
dc.subjectsecondary metaboliteen_US
dc.subjectprecursor-directed biosynthesisen_US
dc.subjectcycloadditionen_US
dc.subjectnatural producten_US
dc.titlePrecursor-Directed Biosynthesis of Novel Jadomycins and Expansion of the Jadomycin Libraryen_US

Files

Original bundle

Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
Dupuis_Stephanie_MSc_CHEM_August_2010.pdf
Size:
8.63 MB
Format:
Adobe Portable Document Format
Description:

License bundle

Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.69 KB
Format:
Item-specific license agreed upon to submission
Description: