Dynamic Systems: Evaluation, Screening and Synthetic Application | Sakulsombat Morakot 1978- , KTH, Organisk kemi

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Dynamic Systems: Evaluation, Screening and Synthetic Application

Title: Trita-CHE-Report

Description:

The research work reported in the thesis deals with the development of dynamic covalent systems and their applications in evaluation and screening of protein-ligands and enzyme inhibitors, as well as in synthetic methodologies. The thesis is divided into four parts as described below.

In part one, synthetic methodologies to access 3-functionalized phthalides and 3-thioisoindolinones using the concept of cascade reactions are demonstrated. Efficient syntheses of the target products are designed and performed in one-pot process under mild reaction conditions.

In part two, phosphine-catalyzed disulfide metathesis for the generation of dynamic carbohydrate system in aqueous solution is demonstrated. In the presence of biological target (Concanavalin A), the optimal dynamic ligand is successfully identified in situ by the ¹H STD-NMR spectroscopy.

In part three, lipase-catalyzed resolutions of dynamic reversible systems using reversible cyanohydrin and hemithioacetal reactions in one-pot processes are demonstrated. The dynamic systems are generated under thermodynamic control in organic solution and subsequently resolved by lipase-mediated resolution under kinetic control. The resolution processes resulted in the lipase-selected substrates with high structural and stereochemical specificities.

In the last part, dynamic fragment-based strategy is presented using β-galactosidase as a model target enzyme. Based on our previous study, the best dynamic inhibitor of β-galactosidase was identified using ¹H STD-NMR technique from dynamic hemithioacetal systems. The structure of the dynamic inhibitor is tailored by fragment linking and optimization processes. The designed inhibitor structures are then synthesized and tested for inhibition activities against β-galactosidase.

; QC 20110526; Härtill 6 uppsatser; Diss. (sammanfattning) Stockholm : Kungliga Tekniska högskolan, 2011; degree of Doctor in Technology; Teknologie doktorsexamen; F3, KTH, Lindstedtsvägen 26, KTH, Stockholm; EU, Europeiska forskningsrådet [MRTN-CT-2006-035614]

Creator:

Sakulsombat Morakot 1978- , KTH, Organisk kemi

Contributor: Ramström Olof Professor; Lüning Ulrich; KTH Skolan för kemivetenskap (CHE) Kemi Organisk kemi

Date: 2011; 2011-06-07T10:00:00; 2011-05-26T11:17:00; http://semium.org/time/2011

Type: science; vet; Other academic; Övrigt vetenskapligt; Annet vitenskapelig; comprehensiveDoctoralThesis; dok; Doctoral thesis, comprehensive summary; Doktorsavhandling, sammanläggning; Doktoravhandling, med artikler; dissertation; text; http://www.eionet.europa.eu/gemet/concept/7472; http://www.eionet.europa.eu/gemet/concept/13026

Format: electronic69; electronic; 69

Identifier: 978-91-7415-986-8; url: http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-34100; 1654-1081; 2011:33

Relation: Trita-CHE-Report1654-10812011:33

Language: eng

Publisher: KTH Royal Institute of Technology

Data provider: Uppsala Universitet

Provider: The European Library

Providing country: Sweden

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