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Title: High-throughput synthesis and screening of chiral stationary phase media
Author: Milnes, Phillip
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2008
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Libraries of peptide based chiral stationary phases (CSPs), using silica-supports, were developed. The CSPs were packed into columns and tested for their ability to resolve racemates using a range of test analytes. The research focused on varying the CSP end group and results show that the most important was 3,5-dinitrobenzoyl. Furthermore, CSPs were developed that used 3,5-dinitrophenylalanine; an amino acid variant of the 3,5-dinitrobenzoyl group, in the peptide core. However, these CSP were found to be unsuccessful in separating the test analytes. Protein chiral stationary phase ligands were screened with a surface plasmon resonance biosensor (Biacore S51), using pharmaceutical enantiomers as analytes, to obtain binding characteristics. Furthermore, these results correlated well with the analogous screenings carried out on HPLC. A reciprocally designed CSP based on a single enantiomer of anthryl ethanol was synthesised, the key step involved the use of Sharpless asymmetric dihydroxylation which incorporated optical character into the molecule. The enantiomer was attached to a silica support and used as a CSP to separate peptide racemates.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available