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Racemisation in chemistry and biology

Ballard, Andrew, Narduolo, Stefania, Ahmad, Hiwa O., Keymer, Nathaniel I, Asaad, Nabil, Cosgrove, David A., Buurma, Niklaas J. and Leach, Andrew G 2019. Racemisation in chemistry and biology. Chemistry - A European Journal 10.1002/chem.201903917

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Abstract

The two enantiomers of a compound often have profoundly different biological properties and so their liability to racemisation in aqueous solutions is an important piece of information. We have reviewed the available data concerning the process of racemisation in vivo, in the presence biological molecules (e.g. racemase enzymes, serum albumin, cofactors and derivatives) and under purely chemical but aqueous conditions (acid, base and other aqueous systems). Mechanistic studies are described critically in light of reported kinetic data. The types of experimental measurement that can be used to effectively determine rate constants of racemisation in various conditions are discussed and the data they provide is summarised. The proposed origins of enzymatic racemisation are presented and suggest ways to promote the process that are different from processes taking place in bulk water. Experimental and computational studies that provide understanding and quantitative predictions of racemisation risk are also presented.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Advanced Research Computing @ Cardiff (ARCCA)
Publisher: Wiley
ISSN: 0947-6539
Date of First Compliant Deposit: 3 January 2020
Date of Acceptance: 28 October 2019
Last Modified: 27 Nov 2020 12:54
URI: http://orca.cf.ac.uk/id/eprint/128177

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