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Imprinted polymers and templated cyclic peptides : a combinatorial approach

Imprinted polymers and templated cyclic peptides : a combinatorial approach
Imprinted polymers and templated cyclic peptides : a combinatorial approach

The aims of this project were to apply the concept of combinatorial chemistry to two fields of supramolecular chemistry: molecular imprinted polymers (MIPs) and metal templated cyclo-oligomerisation of peptides.

A library of MIPs were synthesised as thin films.  A range of aromatic and alkyl acrylamide monomer building blocks were synthesised and the binding properties of the polymers were investigated as a function of the polymerisation mixture.  New screening methods were investigated to allow high-throughput screening of the MIPs.  The results suggested the mixture methacrylic acid-toluene could give efficient MIPs.

Potential molecular imprinted polymers were prepared, by bulk polymerisation and used as HPLC stationary phases.  The properties of the polymers were investigated by resolution of the template and its enantiomer under a number of different elution conditions.  Mobile phases with trifluoroacetic acid improved the resolution, but longer columns or high flow rate prevented base line resolution.

A range of dipeptides were synthesised and used in template mediated synthesis.  The rates of peptide couplings around the metal ion, in solution and on solid support, were investigated as a function of the chain length and nature of the residues of the linear precursor.  Although cyclo-oligomerisations were expected, only linear tetrapeptides were observed in the presence of the metal ion.

University of Southampton
Le Strat, Loïc
Le Strat, Loïc

Le Strat, Loïc (2002) Imprinted polymers and templated cyclic peptides : a combinatorial approach. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

The aims of this project were to apply the concept of combinatorial chemistry to two fields of supramolecular chemistry: molecular imprinted polymers (MIPs) and metal templated cyclo-oligomerisation of peptides.

A library of MIPs were synthesised as thin films.  A range of aromatic and alkyl acrylamide monomer building blocks were synthesised and the binding properties of the polymers were investigated as a function of the polymerisation mixture.  New screening methods were investigated to allow high-throughput screening of the MIPs.  The results suggested the mixture methacrylic acid-toluene could give efficient MIPs.

Potential molecular imprinted polymers were prepared, by bulk polymerisation and used as HPLC stationary phases.  The properties of the polymers were investigated by resolution of the template and its enantiomer under a number of different elution conditions.  Mobile phases with trifluoroacetic acid improved the resolution, but longer columns or high flow rate prevented base line resolution.

A range of dipeptides were synthesised and used in template mediated synthesis.  The rates of peptide couplings around the metal ion, in solution and on solid support, were investigated as a function of the chain length and nature of the residues of the linear precursor.  Although cyclo-oligomerisations were expected, only linear tetrapeptides were observed in the presence of the metal ion.

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Published date: 2002

Identifiers

Local EPrints ID: 464993
URI: http://eprints.soton.ac.uk/id/eprint/464993
PURE UUID: 6286d397-105e-4cd2-879c-7dfb39a302b9

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Date deposited: 05 Jul 2022 00:15
Last modified: 05 Jul 2022 03:51

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Contributors

Author: Loïc Le Strat

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