The c-f bond as a tool for controlling molecular conformation. the preparation and conformational analysis of beta-fluoroamides

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Project objective

The C-F bond is the most polar bond in organic chemistry. Unlike other carbon to halogen bonds, they are strong and unreactive. When C-F bonds are introduced into organic compounds they adopt preferred conformations relative to other functional groups as a consequence of stereoelectronic effects. Recent research indicates that the C.F bond can be used as a design tool to influence the preferred conformation of biologically significant molecules, such as peptides. It should be noted of course that the fluorine atom is sterically small and only a little larger than hydrogen, thus the replacement of the research objectives are: - The synthesis of enantiomerically pure alpha-fluoro-Beta-alanine from L-asparagine. The route will follow literature chemistry until the final step, witch will involve a diazotisation/HF reaction. - Preparation of short peptides using this fluorinated amino acid. The methods will follow standard amino acid/peptide protection deprotection protocols. - An analysis of the conformation of the prepared peptides will be carried out using NMR methods and where appropriate X-ray crystal structure analysis ( of short di and tri peptides) as well as CD. The programme will be experimentally challenging, but it should demonstrate a powerful role for fluorine in medicinal and pharmaceutical chemistry.

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Participants

• UNIVERSITY OF ST ANDREWS · ST ANDREWSCoordinatorUnited Kingdom

Links

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