In April 2016 Manchester eScholar was replaced by the University of Manchester’s new Research Information Management System, Pure. In the autumn the University’s research outputs will be available to search and browse via a new Research Portal. Until then the University’s full publication record can be accessed via a temporary portal and the old eScholar content is available to search and browse via this archive.

Related resources

University researcher(s)

    Synthesis and Sequestrating Properties of Enterochelin Analogues

    Khan, Mohammad

    [Thesis]. Manchester, UK: The University of Manchester; 2019.

    Access to files

    Abstract

    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.

    Bibliographic metadata

    Type of resource:
    Content type:
    Form of thesis:
    Type of submission:
    Degree type:
    Master of Science by Research
    Degree programme:
    MSc by Research Chemistry
    Publication date:
    Location:
    Manchester, UK
    Total pages:
    67
    Abstract:
    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.
    Thesis main supervisor(s):
    Thesis co-supervisor(s):
    Language:
    en

    Institutional metadata

    University researcher(s):

    Record metadata

    Manchester eScholar ID:
    uk-ac-man-scw:322603
    Created by:
    Khan, Mohammad
    Created:
    26th November, 2019, 00:15:31
    Last modified by:
    Khan, Mohammad
    Last modified:
    23rd December, 2019, 12:17:24

    Can we help?

    The library chat service will be available from 11am-3pm Monday to Friday (excluding Bank Holidays). You can also email your enquiry to us.