Abstract
This thesis is divided into seven chapters, which can all be read individually. The
first chapter, however, contains a general introduction to the chemistry used in the
remaining six chapters, and it is therefore recommended to read chapter one before
reading the other chapters.
Chapter 1 is a general introductory chapter for the whole thesis. The history and
concepts of dynamic combinatorial chemistry are described, as are some of the new
and intriguing results recently obtained. Finally, the properties of a broad range of
hexameric macrocycles are described in detail.
Chapter 2 gives a thorough walk-through of a particular dynamic combinatorial
library containing the naturally occurring vitamin B7, also known as d-biotin. This
library is shown to produce a 6 + 6 hexameric structure, denoted biotin[6]uril, which is
able to bind anions in water. Lastly, a dynamic combinatorial library containing both
d-biotin and ethylene urea is described, from which a mixed hexameric macrocyle is
produced due to recognition of bromide anions.
Chapters 3 and 4 describe work on the optimisation of the anion binding properties
of biotin[6]uril by oxidation of the sulfides in the macrocycle. The synthetic procedure
is described together with the anion binding capabilities of the thus created hexameric
macrocycles, biotinsulfoxide[6]uril and biotinsulfone[6]uril, using both calculations and
in situ experiments.
Chapter 5 tells the story of the biotin[6]uril hexaesters and their ability to transport
anions over cell membranes. This transport is found to be selective for chloride
over bicarbonate and sulfate anions. Also anion transport by biotin[6]uril hexaester
analogues are tested.
Chapter 6 contains an evaluation of the anion binding properties of hexameric
macrocycles based on the hemicucurbit[6]uril scaffold. The thermodynamic aspects
of the anion binding in water is evaluated and several factors, e.g. the non-classical
hydrophobe effect and the chaotrope effect, are speculated to be responsible for this
particular behaviour in water.
Chapter 7 describes work on a dynamic combinatorial library containing dendronised
building blocks. The libraries are shown to be at thermodynamic equilibrium,
and different templates are tested towards recognition in the dynamic combinatorial
libraries. Especially, the Bovine Serum Albumin is found to show interesting changes
upon addition to the library, and this is described in detail in the last part of the
chapter.
first chapter, however, contains a general introduction to the chemistry used in the
remaining six chapters, and it is therefore recommended to read chapter one before
reading the other chapters.
Chapter 1 is a general introductory chapter for the whole thesis. The history and
concepts of dynamic combinatorial chemistry are described, as are some of the new
and intriguing results recently obtained. Finally, the properties of a broad range of
hexameric macrocycles are described in detail.
Chapter 2 gives a thorough walk-through of a particular dynamic combinatorial
library containing the naturally occurring vitamin B7, also known as d-biotin. This
library is shown to produce a 6 + 6 hexameric structure, denoted biotin[6]uril, which is
able to bind anions in water. Lastly, a dynamic combinatorial library containing both
d-biotin and ethylene urea is described, from which a mixed hexameric macrocyle is
produced due to recognition of bromide anions.
Chapters 3 and 4 describe work on the optimisation of the anion binding properties
of biotin[6]uril by oxidation of the sulfides in the macrocycle. The synthetic procedure
is described together with the anion binding capabilities of the thus created hexameric
macrocycles, biotinsulfoxide[6]uril and biotinsulfone[6]uril, using both calculations and
in situ experiments.
Chapter 5 tells the story of the biotin[6]uril hexaesters and their ability to transport
anions over cell membranes. This transport is found to be selective for chloride
over bicarbonate and sulfate anions. Also anion transport by biotin[6]uril hexaester
analogues are tested.
Chapter 6 contains an evaluation of the anion binding properties of hexameric
macrocycles based on the hemicucurbit[6]uril scaffold. The thermodynamic aspects
of the anion binding in water is evaluated and several factors, e.g. the non-classical
hydrophobe effect and the chaotrope effect, are speculated to be responsible for this
particular behaviour in water.
Chapter 7 describes work on a dynamic combinatorial library containing dendronised
building blocks. The libraries are shown to be at thermodynamic equilibrium,
and different templates are tested towards recognition in the dynamic combinatorial
libraries. Especially, the Bovine Serum Albumin is found to show interesting changes
upon addition to the library, and this is described in detail in the last part of the
chapter.
| Original language | English |
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| Publisher | Department of Chemistry, Faculty of Science, University of Copenhagen |
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| Number of pages | 220 |
| Publication status | Published - 2015 |