Synthesis and Sequestrating Properties of Enterochelin Analogues
General Material Designation
[Thesis]
First Statement of Responsibility
Khan, Mohammad
Subsequent Statement of Responsibility
Quayle, Peter
.PUBLICATION, DISTRIBUTION, ETC
Name of Publisher, Distributor, etc.
The University of Manchester (United Kingdom)
Date of Publication, Distribution, etc.
2019
GENERAL NOTES
Text of Note
68 p.
DISSERTATION (THESIS) NOTE
Dissertation or thesis details and type of degree
M.S.
Body granting the degree
The University of Manchester (United Kingdom)
Text preceding or following the note
2019
SUMMARY OR ABSTRACT
Text of Note
Acquisition of iron by siderophores is critical for the survival of many microbes. Enterochelin is a catechol siderophore that has a trilactonate macrocylic core derived from serine that is connected to three 2, 3-dihydroxybenzoyl moieties all of which participate in the coordination of an iron atom in a hexadentate fashion. The work described in this thesis is concerned with the development of a viable synthetic pathway to a sulfonamide enterochelin analogue. Starting with L-Serine methyl ester hydrochloride and with the use of 2,2-dibutyl-1,3,2-dioxastannolane a synthetic pathway has been optimised for the synthesis of 3S,7S,11S)-3,7,11-tris(tritylamino)-1,5,9-trioxacyclododecane-2,6,10-trione enabling routine preparation on a multi-gram scale. Improvements have been made to the synthetic pathway towards the synthesis of 2,3-dimethoxybenzenesulfonyl chloride including a one-step conversion of tert-butyl (2,3-dimethoxyphenyl) carbamate to 2,3-dimethoxyanaline hydrochloride using HCl in dioxane.