Studies towards synthetic receptors for small peptides
Studies towards synthetic receptors for small peptides
This thesis is concerned with the design and synthesis of novel receptors capable of recognising simple dipeptides. The aim of the work described herein was to develop an incremental approach to the complex problem of peptide recognition, leading to ever more selective and sophisticated receptors. The initial target chosen for the recognition studies was receptor 1, which features an aza crown ether to provide a high degree of assured binding for the ammonium or carboxylate terminus of the peptide, an amide side-wall to develop further hydrogen bonding interactions with the guest and a rigid biaryl spacer to provide an open cavity. vskip 3.0cm
Chapters 2 and 3 describe several of the approaches undertaken towards the synthesis of the desired macrocycle 1. Chapter 4 deals with the successful synthesis of the macrocycle 1 using a novel 4,4' intramolecular biaryl formation as the cyclisation step. Finally Chapter 5 discusses the molecular modelling studies carried out to assess the recognition potential of these receptors for simple dipeptides, along with the binding studies undertaken with a series of simple substrates using mass spectrometry experiments. Through the application of molecular modelling we are able to propose some possible modes of binding of this receptor to the potassium carboxylate salts of N-acetyl glycine and N-acetyl β alanine.
University of Southampton
1994
Patel, Hitesh Kumar
(1994)
Studies towards synthetic receptors for small peptides.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis is concerned with the design and synthesis of novel receptors capable of recognising simple dipeptides. The aim of the work described herein was to develop an incremental approach to the complex problem of peptide recognition, leading to ever more selective and sophisticated receptors. The initial target chosen for the recognition studies was receptor 1, which features an aza crown ether to provide a high degree of assured binding for the ammonium or carboxylate terminus of the peptide, an amide side-wall to develop further hydrogen bonding interactions with the guest and a rigid biaryl spacer to provide an open cavity. vskip 3.0cm
Chapters 2 and 3 describe several of the approaches undertaken towards the synthesis of the desired macrocycle 1. Chapter 4 deals with the successful synthesis of the macrocycle 1 using a novel 4,4' intramolecular biaryl formation as the cyclisation step. Finally Chapter 5 discusses the molecular modelling studies carried out to assess the recognition potential of these receptors for simple dipeptides, along with the binding studies undertaken with a series of simple substrates using mass spectrometry experiments. Through the application of molecular modelling we are able to propose some possible modes of binding of this receptor to the potassium carboxylate salts of N-acetyl glycine and N-acetyl β alanine.
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Published date: 1994
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Local EPrints ID: 462622
URI: http://eprints.soton.ac.uk/id/eprint/462622
PURE UUID: fb02a437-a9c3-4677-883b-b76c3e1369f9
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Date deposited: 04 Jul 2022 19:32
Last modified: 04 Jul 2022 19:32
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Author:
Hitesh Kumar Patel
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