Isolation, structure, synthesis, and biosynthesis of selected bioactive microbial metabolites

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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Staley, Andrew Lawrence

Contributors dc:contributor

• Rinehart, Kenneth L., Jr.

• Chemistry, Organic

Statement dc:rights

• Copyright 1990 Staley, Andrew Lawrence

Language dc:language

eng

Identifier

AAI9021762
(UMI)AAI9021762

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/22041