The industrial scale application of baker’s yeast mediated reductions of prochiral α,β-unsaturated aldehydes is usually hindered by discouragingly low productivities. Exploiting the recently developed synergic application of the in situ substrate-feeding-product-removal (SFPR) technique together with recombinant isolated enzymes (enoate reductases and alcohol dehydrogenases), it was possible to achieve a 50-fold improvement of the productivity of the biocatalytic enantioselective reduction of alphabrocine to the corresponding optically active bromohydrin (98% ee). The latter was then employed in the synthesis of the active enantiomer of the appetite suppressant drug (R)-2-benzylmorpholine.
Productivity enhancement of biocatalysed enantioselective C=C reductions: the bioreduction of alphabrocine from whole cells to isolated enzymes
PARMEGGIANI, FABIO
2011-01-01
Abstract
The industrial scale application of baker’s yeast mediated reductions of prochiral α,β-unsaturated aldehydes is usually hindered by discouragingly low productivities. Exploiting the recently developed synergic application of the in situ substrate-feeding-product-removal (SFPR) technique together with recombinant isolated enzymes (enoate reductases and alcohol dehydrogenases), it was possible to achieve a 50-fold improvement of the productivity of the biocatalytic enantioselective reduction of alphabrocine to the corresponding optically active bromohydrin (98% ee). The latter was then employed in the synthesis of the active enantiomer of the appetite suppressant drug (R)-2-benzylmorpholine.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
