Synthesis and evaluation of new solid supports for solid phase organic synthesis
Synthesis and evaluation of new solid supports for solid phase organic synthesis
The aims of this project were the preparation, characterisation and application of a series of non-grafted polystyrene resins containing a styrenic poly(ethylene glycol) derivative. The resins were designed to balance swelling and solvation with improved handling issues. The monomer, 1-[2-(2-methoxyethoxy)ethoxy-4-vinyl-benzene, containing an inert phenyl ether linkage designed to provide wide chemical compatibility and stability, was prepared on a large scale following a four-step procedure. A range chloromethylstyrene functionalised resins with DVB cross-linking from 2% to 7% and PEG monomer loading from 5% to 40% were prepared by suspension co-polymerisation. A multiple-parallel approach to the preparation of resins in suspension polymerisation was applied using a novel system that allowed fast optimisation and preparation of new solid supports. The resulting resins were tested in terms of swelling properties in a range of different solvents and chemical stability to strong acid/base conditions. The synthetic performances of the new resins were compared to those of TentaGelTM, AgroGelTM and aminomethyl PS by performing the synthesis of small model peptides, biaryl derivatives via Suzuki coupling and arylethers via Mitsunobu reaction.
Relative to traditional PEG-grafted resins, these PEG-based resins have a much higher loading capacity while maintaining broad solvent compatibility. The co-polymers were stable to strongly acidic/basic conditions and a range of physical manipulations. The new resins proved to be highly suitable for peptide synthesis, Suzuki and Mitsunobu couplings having improved performance over TentaGelTM and Merrifield type resins.
University of Southampton
Alesso, Sonia Maria
25342c06-e296-480a-8d71-6b434e906b98
2002
Alesso, Sonia Maria
25342c06-e296-480a-8d71-6b434e906b98
Alesso, Sonia Maria
(2002)
Synthesis and evaluation of new solid supports for solid phase organic synthesis.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The aims of this project were the preparation, characterisation and application of a series of non-grafted polystyrene resins containing a styrenic poly(ethylene glycol) derivative. The resins were designed to balance swelling and solvation with improved handling issues. The monomer, 1-[2-(2-methoxyethoxy)ethoxy-4-vinyl-benzene, containing an inert phenyl ether linkage designed to provide wide chemical compatibility and stability, was prepared on a large scale following a four-step procedure. A range chloromethylstyrene functionalised resins with DVB cross-linking from 2% to 7% and PEG monomer loading from 5% to 40% were prepared by suspension co-polymerisation. A multiple-parallel approach to the preparation of resins in suspension polymerisation was applied using a novel system that allowed fast optimisation and preparation of new solid supports. The resulting resins were tested in terms of swelling properties in a range of different solvents and chemical stability to strong acid/base conditions. The synthetic performances of the new resins were compared to those of TentaGelTM, AgroGelTM and aminomethyl PS by performing the synthesis of small model peptides, biaryl derivatives via Suzuki coupling and arylethers via Mitsunobu reaction.
Relative to traditional PEG-grafted resins, these PEG-based resins have a much higher loading capacity while maintaining broad solvent compatibility. The co-polymers were stable to strongly acidic/basic conditions and a range of physical manipulations. The new resins proved to be highly suitable for peptide synthesis, Suzuki and Mitsunobu couplings having improved performance over TentaGelTM and Merrifield type resins.
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Published date: 2002
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Local EPrints ID: 464910
URI: http://eprints.soton.ac.uk/id/eprint/464910
PURE UUID: f4c5c2d7-fdd1-4ba1-9aab-e7f3d630fe48
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Date deposited: 05 Jul 2022 00:09
Last modified: 16 Mar 2024 19:49
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Author:
Sonia Maria Alesso
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