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Key Factors for Multivalency Effects in Carbohydrate Nanoplatform-Lectin Interactions
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-211488OAI: oai:DiVA.org:kth-211488DiVA, id: diva2:1129735
Funder
EU, FP7, Seventh Framework Programme, 289033
Note

QC 20170809

Available from: 2017-08-07 Created: 2017-08-07 Last updated: 2017-08-09Bibliographically approved
In thesis
1. Metals in Dynamic Chemistry: Selection & Catalysis
Open this publication in new window or tab >>Metals in Dynamic Chemistry: Selection & Catalysis
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In the adaptation to the oxidative environment on earth, metals played a crucial role for the evolution of life. The presence of metals also allowed access to advanced functions due to their unique coordination sphere and reactivity. This thesis focused on exploiting these unique properties for further development of the field of dynamic chemistry – a field in which adaptation plays a central role as well.

The first part of the thesis aimed to create a better understanding of multivalent effects in carbohydrate-lectin interactions. By reversible ligand coordination to zinc ions one of the nanoplatforms, the Borromean rings, could be selectively obtained. After carbohydrate functionalization the binding events were monitored by quartz crystal microbalance technology and compared to glycosylated fullerenes and dodecaamide cages. Overall, this investigation indicated that statistical and polyelectrolyte effects play a considerable role in the observed multivalent effects.

The second part of the thesis aimed to design and synthesize a new catalyst for application in aqueous olefin metathesis. This afforded a ruthenium based catalyst that was applied in the self- and cross-metathesis of highly functionalized substrates, such as carbohydrates. In addition, it was shown that addition of a small amount of acetic acid prevented undesired double bond isomerization.

The last part of the thesis aimed to explore new methods to discover transition metal catalysts. Dynamic exchange of directing groups generated a pool of potential substrates for C-H activation. Combining this pool of substrates with a pool of potential catalysts resulted in amplification of a reactive substrate/metal combination. By iterative deconvolution in combination with mass spectrometry, this “intermediate” could be identified from the mixture, proving applicability of this alternative approach to catalyst discovery.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2017. p. 71
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2017:32
Keywords
constitutional dynamic chemistry, selection, multivalent interactions, carbohydrates, quartz crystal microbalance, catalyst screening, aqueous olefin metathesis, C-H activation
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-211492 (URN)978-91-7729-470-2 (ISBN)
Public defence
2017-09-08, Sal F3, Lindstedtsvägen 26, Stockholm, 09:00 (English)
Opponent
Supervisors
Funder
EU, FP7, Seventh Framework Programme, 289033
Note

QC 20170809

Available from: 2017-08-09 Created: 2017-08-07 Last updated: 2017-08-18Bibliographically approved

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