Studies towards novel aldolase mimics
2009
The present thesis is concerned with a novel approach towards the design of
artificial aldolase mimics.
The introductory chapter provides an overview of previous strategies and
approaches that have been employed in the design and synthesis of artificial
enzyme systems.
Following on from a brief introduction to previous work within our own group,
Chapter 2 presents and discusses the preparation and reactivity of a number of
novel polymeric systems which are capable of catalysing the aldol reaction. The
strategy adopted consisted of the preparation of regiochemically defined
alternating co-polymers wherein each of the two monomers, an N-alkylated
maleimide and a para carboxamide styrene possessed either a carboxylic acid or
an amino group and were hence capable of functioning as Class I aldolase
mimetics.
A complementary strategy has also been undertaken wherein both functional
groups involved in catalysis are attached to a single monomer, and subsequently
subjected to ring opening metathesis polymerisation. This approach guaranteed
attachment of these two groups in a fixed 1:1 ratio and had the added advantage of
acting as organocatalysts in their own right. For this purpose, systems based on 7-
azabicyclo[2.2.1]hept-2-ene, tropane alkaloid like derivatives and a functionalised
norbornene were studied. Preliminary work towards functionalised bispidinone
derivatives were also considered within this framework.
Chapter 3 provides a formal description of the detailed experimental results and
procedures used.
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