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" Synthesis and Sequestrating Properties of Enterochelin Analogues "
Khan, Mohammad
Quayle, Peter
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Latin Dissertation
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| Language of Document
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English
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| Record Number
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1106688
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| Doc. No
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TLpq2408879212
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| Main Entry
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Khan, Mohammad
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Quayle, Peter
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| Title & Author
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Synthesis and Sequestrating Properties of Enterochelin Analogues\ Khan, MohammadQuayle, Peter
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| College
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The University of Manchester (United Kingdom)
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| Date
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2019
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| student score
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2019
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| Degree
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M.S.
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| Page No
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68
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| Abstract
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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.
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Biochemistry
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Chemistry
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