The biocatalytic anti-Prelog stereoselective reduction of 4-(trimethylsilyl)-3-butyn-2-one to (R)-4-(trimethylsilyl)-3-butyn-2-ol, a key chiral block for the synthesis of (R)-benzyl-4-hydroxyl-2-pentynoate with the potential therapeutical function for Alzheimer's disease, with a novel strain Acetobacter sp. CCTCC M209061 isolated from China kefir was successfully conducted in an ionic liquid (IL)-containing system. Various hydrophilic ILs exerted widely different effects on the bioreduction. While the cells lost their activity dramatically in BF4-- or TfO--based ILs, they displayed excellent catalytic and sugar metabolic activities in 1-(2'-hydroxyl) ethyl-3-methylimidazolium nitrate (C2OHMIM�NO3). Besides, the better biocompatible IL C2OHMIM�NO3 was found to be able to modify the cells' membrane permeability, enhancing the product transportation out of the cells, thus partly relieving its inhibitory and toxic effects. In C2OHMIM�NO3-containing system, the initial reaction rate, maximum yield and product e.e. were 1.7 �mol/min,91% and 99% above, respectively, which are much higher than those with aqueous system.

Use of a hydrophilic ionic liquid to improve biocatalytic asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one with a newly isolated strain <i>Acetobacter </i> sp. CCTCC M209061

242nd National Meeting (2011)

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Use of a hydrophilic ionic liquid to improve biocatalytic asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one with a newly isolated strain Acetobacter sp. CCTCC M209061