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Rinehart, Kenneth L., Jr. Staley, Andrew Lawrence 2011-05-07T13:27:04Z 2011-05-07T13:27:04Z 10000-01-01 1990 The biosynthetic origin of the $meta$-C$\sb7$N unit of the naphthoquinoid chromophore of the streptovaricins was shown to be 3-amino-5-hydroxybenzoic acid (AHBA) through carbon-14 and carbon-13 labeling studies. ($Carboxy$-$\sp{14}$C) AHBA was incorporated at a rate of 0.1% into streptovaricin C, and ($carboxy$-$\sp{13}$C) AHBA gave an enrichment factor of 21 for the resonance corresponding to the C-21 carbonyl in the $\sp{13}$C NMR spectrum of labeled streptovaricin C. The optimization of incorporation of labeled glucose and the production of mutants of Streptomyces spectabilis are also discussed. A detailed analysis of the $\sp1$H and $\sp{13}$C NMR spectra of streptovaricin C is described. Two new series of metabolic products were isolated from modified culture broths of S. spectabilis. The first series of compounds were members of the aureolic acid class of antibiotics and were trivially named the spectomycins. The compounds were isolated as monomeric and dimeric forms of the same chromophore structure. The second series of compounds proved to be cyclic depsipeptides that were closely related to the monamycins, but differed from the latter by one oxygen atom. The new compounds were trivially named the deoxymonamycins. The synthesis of the iron-chelating siderophore pyochelin, isolated from Pseudomonas aeruginosa, was reinvestigated, and a significant improvement in the overall yield of four of the eight possible diastereomers of the compound was realized. The relative and absolute stereochemistry of the four diastereomers was assigned through a combination of spectroscopic, crystallographic, and chemical analyses. Made available in DSpace on 2011-05-07T13:27:04Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9021762.pdf: 8133509 bytes, checksum: fb1ea13559ab4185ecdfd1ed7e203ba9 (MD5) Previous issue date: 1990 Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:54:55Z Item is restricted indefinitely. Restriction data tranferred 2014-07-01T11:25:34-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission ETDs are only available to UIUC Users without author permission U of I Only AAI9021762 (UMI)AAI9021762 http://hdl.handle.net/2142/22041 eng Copyright 1990 Staley, Andrew Lawrence Chemistry, Organic Isolation, structure, synthesis, and biosynthesis of selected bioactive microbial metabolites text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.