Abstract
Currently, the power and usefulness of biocatalysis in organic synthesis is undeniable, mainly due to the very high enantiomeric excess reached using enzymes, in an attempt to emulate natural processes. However, the use of isolated enzymes has some significant drawbacks, the most important of which is cost. The use of whole cells has emerged as a useful strategy with several advantages over isolated enzymes; for this reason, modern research in this field is increasing, and various reports have been published recently. This review surveys the most recent developments in the enantioselective reduction of carbon-carbon double bonds and prochiral ketones and the oxidation of prochiral sulfides using whole cells as biocatalytic systems.
Highlights
The enantioselective synthesis of organic compounds is one of the greatest challenges in organic chemistry, mainly because of its importance in the development of compounds with biological activity as current drugs or potential new drugs
Most publications on biocatalysis focus on isolated enzymes obtained by the overexpression of enzymes in genetically engineered microorganisms; the use of these biocatalysts is expensive and requires special techniques and resources, such as auxiliary enzymes to renew the cofactors or cloning techniques, respectively [5,6]
4–6 days of by the same group [28,29], who previously published studies on the regioselective bioreduction incubation, with e.e. values of greater than 98%. These results correlated with the findings reported of the conjugated double bond of (S)-perillaldehyde (15), finding that Euglena gracilis- and bakers by the same group [28,29], who previously published studies on the regioselective bioreduction of yeast-mediated biotransformation of this compound produced a mixture of unsaturated and saturated the conjugated double bond of (S)-perillaldehyde
Summary
The enantioselective synthesis of organic compounds is one of the greatest challenges in organic chemistry, mainly because of its importance in the development of compounds with biological activity as current drugs or potential new drugs With this aim, several catalytic processes have been reported, such as reactions with transition metal catalysts, organic catalysts and biological catalysts. Most publications on biocatalysis focus on isolated enzymes obtained by the overexpression of enzymes in genetically engineered microorganisms; the use of these biocatalysts is expensive and requires special techniques and resources, such as auxiliary enzymes (increasing the cost) to renew the cofactors or cloning techniques, respectively [5,6] Even if these approaches are important alternatives, they are not commonly used in laboratories investigating organic synthesis. This review surveys recent developments in biocatalysis using whole cells; it begins with a presentation of the evolution of the concept in the first section, followed by a detailed description of applications in asymmetric reactions, such as the reduction of C=C bonds, reduction of prochiral ketones, oxidation of sulfides to chiral sulfoxides, and some other less common transformations, while focusing the developments reported in the last ten years
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