Biosynthetic Studies on Pactamycin

Pactamycin (1), a cytotoxic antibiotic produced by Streptomyces pactum, var. pactum, contains several interesting structural features, including a cyclopentanoid ring, which is rare among natural products, a 6-methylsalicylic acid (6-MSA) unit derived from acetate via a polyketide route, and a m-aminoacetophenone unit, which represents the m-C$\sb7$N unit found in many antibiotics. It was expected that 6-MSA would be an advanced precursor to the corresponding unit on pactamycin, but feeding experiments with 6-methyl (carboxy-$\sp $C) salicylic acid and methyl 6-methyl (carboxy-$\sp $C) salicylate failed to show significant incorporation into either pactamycin or its analogue pactamycate. In addition, these precursors were apparently toxic to S. pactum, causing pronounced acidification of the production medium and substantial reduction of pactamycin production.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)

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

2014

Author dc:creator

• Adams, Erik Stuart

Contributors dc:contributor

• Rinehart, Kenneth L., Jr.

• Biology, Microbiology
• Chemistry, Organic

Identifier

(UMI)AAI9328955

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/72281