6169-06-8Relevant articles and documents
Supported ionic liquid-like phases as efficient solid ionic solvents for the immobilisation of alcohol dehydrogenases towards the development of stereoselective bioreductions
Altava, Belen,García-Verdugo, Eduardo,Gotor-Fernández, Vicente,Lavandera, Iván,Lozano, Pedro,Luis, Santiago V.,Porcar, Raul
, p. 5609 - 5617 (2021/08/16)
Polymeric materials containing ionic liquid fragments, like those found in bulk ILs, are excellent solid media for the immobilisation of biocatalysts. Herein, the entrapment of the enzymatic system formed by alcohol dehydrogenase from Rhodococcus ruber (ADH-A) overexpressed in E. coli and its coenzyme has been studied. The activity, stability and reusability of these preparations have been investigated in the bioreduction of prochiral ketones finding excellent levels of conversion and selectivity. Interestingly, the immobilised enzyme remained active and exhibited excellent stability in aqueous solutions after several recycling uses. More importantly, these biopolymer materials retained most of their activity after consecutive reaction cycles, prolonged storage and under flow conditions.
Production of chiral alcohols from racemic mixtures by integrated heterogeneous chemoenzymatic catalysis in fixed bed continuous operation
Carceller, Jose Miguel,Climent, Maria J.,Corma, Avelino,Iborra, Sara,Mifsud, Maria
, p. 2767 - 2777 (2020/06/17)
Valuable chiral alcohols have been obtained from racemic mixtures with an integrated heterogeneous chemoenzymatic catalyst in a two consecutive fixed catalytic bed continuous reactor system. In the first bed the racemic mixture of alcohols is oxidized to the prochiral ketone with a Zr-Beta zeolite and using acetone as the hydrogen acceptor. In the second catalytic bed the prochiral ketone is stereoselectively reduced with an alcohol dehydrogenase (ADH) immobilized on a two dimensional (2D) zeolite. In this process, the alcohol (isopropanol) formed by the reduction of acetone in the first step reduces the cofactor in the second step, and the full reaction cycle is in this way internally closed with 100% atom economy. A conversion of about 95% with ~100% selectivity to either the (R) or the (S) alcohol has been obtained for a variety of racemic mixtures of alcohols.
METHODS OF MAKING HIGH ENANTIOSELECTIVE SECONDARY ALCOHOLS
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Paragraph 0098; 0099; 0109, (2020/09/08)
A new process to synthesis of compound OBI-3424 R-form and S-form products is provided. The "R-form" compound OBI-3423 was first synthesized with 48% overall yield from compound OBI-3424-5 by installation of the labile phosphate motif at later stage. The stereo chemistry is established by 5 steps chemo-enzyme combination synthesis to afford 99% optical purity, After then, the "S-form" compound OBI-3424 is prepared with improving overall yield of 54% from compound OBI-3424-5. The stereo chemistry is established by 4 steps combination of chemo-enzyme synthesis with excellent optical purity of 99%.