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Title:Isolation, structure, synthesis, and biosynthesis of selected bioactive microbial metabolites
Author(s):Staley, Andrew Lawrence
Doctoral Committee Chair(s):Rinehart, Kenneth L., Jr.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract: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.
Issue Date:1990
Rights Information:Copyright 1990 Staley, Andrew Lawrence
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9021762
OCLC Identifier:(UMI)AAI9021762

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