for Physical Chemists by Physical Chemists


Configurational Stability of Chiral Compounds

Dr Niek Buurma, Physical Organic Chemistry Group, University of Cardiff

Racemisation of chiral centres in drugs may result in serious problems during drug development and/or drug approval. Kinetic and mechanistic understanding of racemisation processes of some of the most frequently occurring chiral centres in pharmaceuticals will help in avoiding or remediating such problems.

We have synthesised a series of chiral compounds based on phenylglycine and hydantoin scaffolds and studied both racemisation and H/D exchange under various aqueous conditions (pH, buffer concentration, ionic strength, co-solvents, temperature). The results provide insight into reaction mechanisms of racemisation as well as quantitative data on substituent and buffer effects on racemisation reactions.

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Last modified: 28 April 2008