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Solid phase peptide synthesis thesis

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Making Solid-Phase Peptide Synthesis Greener: A Review of the Literature

Making Solid-Phase Peptide Synthesis Greener: A Review of the Literature

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Solid Phase Peptide Synthesis

The purpose of this guide is to provide practical information for planning and executing successful solid phase peptide syntheses. The procedures included were found to be generally applicable, but they may not be optimal in every synthesis. Various factors, including the production scale, peptide sequence and length of the peptide might require modification of these procedures for best results. In critical applications, if time and materials permit, small-scale tests are recommended. Before preparing any peptide on a large scale, it should be synthesized on a small scale first to identify and rectify potential problems.
Linear peptides 13mers were synthesised using solid phase peptide synthesis and 9-fluorenylmethoxycarbonyl Fmoc chemistry. The peptides were assembled on a solid-phase polyethylene glycol-polystyrene support using the "hyper acid labile" linker xanthenoxyvaleric acid and were labelled in situ with 4-[19F]- or 4-[18F]fluorobenzoic acid. This novel method was used to label peptides containing the arginine-glycine-aspartic acid RGD motif, the binding site of many integrins. In vitro studies showed that the fluorobenzoyl prosthetic group had no deleterious effect on the ability of these peptides to inhibit the binding of human cells via integrins. Biodistribution studies in tumour-bearing mice showed that although the linear peptides were rapidly removed from the circulation by the liver and kidneys, there was a transient and non-RGD-dependent accumulation in the tumour of both the test and the control peptides.

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