Synthesis of new citrate-based siderophores as potential drug delivery agents for mycobacterium paratuberculosis and the reactions of n-(benzoyloxy) hexylamine with ketones and aldehydes

Keywords

Siderophores

Abstract

A previously synthesized acinetoferrin imide derivative 4 was shown to facilitate the growth rate of Mycobacterium paratuberculosis just as well as the native chelator, Mycobactin J. The first chapter of the thesis describes the synthesis of several new citratebased siderophores (12, 13) for future biological evaluation as bacterial growth promoters. The overall goal is to use structures, which facilitate bacterial growth, as new vectors to deliver antibiotics. The synthesis involved the construction of a N-(alkylamino}-Nhydroxylcinnamamide precursor via a tandem oxidation-acylation of the primary amino group of a protected diam.inc derivative. This elaboration was completed prior to coupling with the tenninal carboxylic acid groups of citric acid. The effects of structurally-altered siderophores on the growth rate of Mycobacterium paratuberculosis will be evaluated along with Mycobactin J. Acinetoferrin (3) was also resynthesized for comparison purposes. In the second chapter, a short survey of the reactions involving N(benzoyloxy)hexylamine (35) with ketones and aldehydes is described. We anticipated that Baeyer-Villiger type rearrsngements would occur with the R-NHOOCPh system to give tertiary amides. Unfortunately, none of the expected products were observed. It seemed that only decomposition of N-benzoyloxyamine occurred. The mechanism of this type of reaction could not be determined based only on these preliminary trials.

Notes

This item is only available in print in the UCF Libraries. If this is your thesis or dissertation, you can help us make it available online for use by researchers around the world by STARS for more information.

Graduation Date

2000

Advisor

Phanstiel, Otto

Degree

Master of Science (M.S.)

College

College of Arts and Sciences

Department

Chemistry

Format

PDF

Pages

89 p.

Language

English

Length of Campus-only Access

None

Access Status

Masters Thesis (Open Access)

Identifier

DP0028709

Subjects

Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences

Accessibility Status

PDF accessibility verified using Adobe Acrobat Pro accessibility checker.

This document is currently not available here.

Share

COinS