Utilising hardly-water soluble substrates as a second phase enables the straightforward synthesis of chiral alcohols

Reaction Engineering of Biocatalytic Enantioselective Reduction: A Case Study for Aliphatic Ketones

“…In the present investigation, the enantioselectivity of the enzyme was not an issue. In all cases, the measured ee was always ≥99.5% for long-chain aliphatic alcohols, which was in line with previous findings. ,− , …”

“…Alcohol dehydrogenase from Lactobacillus brevis ( Lb ADH, EC 1.1.1.2) exhibits outstanding enantioselectivity, robustness, and flexibility in a wide variety of reaction conditions . The substrate scope of this enzyme is broad, and its ability to convert long-chain aliphatic ketones into the desired ( R )-2-alcohols has been proven in many batch syntheses, , as well as in monophasic, , and biphasic − continuous experiments. Water-solubility restrictions in single-phase approaches can be overcome by applying an ionic liquid (IL) as a solubiliser. ,, Kinetics , and stability tests , reveal the applicability of Lb ADH in many processes.…”

“…In all cases, the measured ee was always ≥99.5% for long-chain aliphatic alcohols, which was in line with previous findings. 1,[19][20][21]33 The cost analysis revealed that cofactor utilisation was the bottleneck of this process. Thus, the target key figures were X R2 , g NADP + consumed /g 2-octanol , and STY, as well as the overall cost.…”

Highly enantioselective bioreduction of 1-(3,4-difluorophenyl)-3-nitropropan-1-one: key intermediate of ticagrelor

“…Medium engineering and modied substrate addition strategies lead to enhanced substrate utilization and play an important role in establishing whole cell processes at industrial scale. [10][11][12] Ticagrelor (Scheme 1, ( 5)) is a novel P 2 Y 12 receptor antagonist which functions by blocking adenosine diphosphate-mediated platelet aggregation. There are several published reports on the synthesis of this carbocyclic nucleoside and analogs, [13][14][15][16] however insufficient research has been targeted on the key chiral intermediate diurophenyl cyclopropylamine (4).…”

Asymmetric reduction of a key intermediate of eslicarbazepine acetate using whole cell biotransformation in a biphasic medium

“…Reaction medium engineering plays an important role in whole-cell based ketone reductions. The use of water miscible organic solvents, 20 non-polar solvents in a biphasic system, 21 ketone substrate as an immiscible phase 22 and neat substrate as a reaction medium 23 have been documented.…”