Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 16, Pages 3179-3190Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300549
Keywords
asymmetric synthesis; cascade reactions; CC bond formation; chiral -hydroxy nitriles; enzyme catalysis; halohydrin dehalogenase; multi-enzymatic biosynthesis; oxidoreductases
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Funding
- Key Project of Chinese National Programs for Fundamental Research and Development [2011CB710800]
- National Natural Science Foundation of China [21076187, 20936002]
- Hi-Tech Research and Development Program of China [2011AA02A209]
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To establish a system for the efficient one bacterial multi-enzymatic biosynthesis of both (R)- and (S)--hydroxy nitriles, we co-expressed alcohol dehydrogenases with opposite stereoselectivities, cofactor regeneration enzymes, and a halohydrin dehalogenase in Escherichia coli. By researching cofactor recycling and various co-expression strategies and by selecting and engineering the halohydrin dehalogenase, we engineered two E. coli strains, which were subsequently used in a cascade of reactions to produce chiral -hydroxy nitriles with high enantiomeric excess directly from prochiral -halo ketones. Three valuable pharmaceutical intermediates were prepared by means of this catalytic system, and substrate conversion reached about >99%. More importantly, the system is of low cost because there is no need for expensive cofactors or for expression and purification of the component enzymes.
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