Novel biocatalyst technology for the preparation of chiral amines

  • Published 2004

Abstract

A new method is emerging as a robust, general and scaleable platform technology for the preparation of optically active chiral amines by deracemisation of racemic mixtures. e technology, which was developed at the University of Edinburgh, Scotland, is now being optimised for industrial application by Ingenza Ltd, an Edinburgh-based bioprocess company. e approach employs the simultaneous use of a highly selective oxidase biocatalyst and a chemical reducing agent or catalyst (Figure 1), and can be used to prepare a wide range of optically pure amines in yields often approaching 100%. e key advantages of the technology lie in the co-ordinated action of already proven industrial catalysts and efficient methods of genetic screening to adapt the approach for the preparation of valuable industrial targets. Enantiomerically pure chiral amines are of increasing commercial value in the fine chemical and pharmaceutical areas in view of their application as resolving agents (1), chiral auxiliaries/chiral bases (2) and catalysts for asymmetric synthesis (3). Moreover, chiral amines often possess pronounced biological activity in their own right, and hence are in significant demand as intermediates for pharmaceuticals (4) and agrochemicals (Figure 2) in an expanding market where revenues due to chiral technologies are expected to reach US$14.9 billion by 2009. However, the current methods used to prepare enantiomerically pure chiral amines are largely based upon the resolution of racemates, either by recrystallisation of diastereomeric salts (5) or by enzyme-catalysed kinetic resolution of racemic substrates using lipases and acylases (6). Resolutions of this type are inherently inefficient (maximum 50% yield) and are increasingly viewed as uneconomic and non-competitive. In order to develop more efficient methods, attention is turning towards asymmetric approaches or their equivalent, for example the asymmetric hydrogenation of imines (7) or the conversion of ketones to amines using transaminases (8). Asymmetric approaches have proven extremely successful in specific instances but,

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Cite this paper

@inproceedings{2004NovelBT, title={Novel biocatalyst technology for the preparation of chiral amines}, author={}, year={2004} }