Abstract
In this review the recent reports of biocatalytic reactions applied to the desymmetrization of meso-compounds or symmetric prochiral molecules are summarized. The survey of literature from 2015 up to date reveals that lipases are still the most used enzymes for this goal, due to their large substrate tolerance, stability in different reaction conditions and commercial availability. However, a growing interest is focused on the use of other purified enzymes or microbial whole cells to expand the portfolio of exploitable reactions and the molecular diversity of substrates to be transformed. Biocatalyzed desymmetrization is nowadays recognized as a reliable and efficient approach for the preparation of pharmaceuticals or natural bioactive compounds and many processes have been scaled up for multigram preparative purposes, also in continuous-flow conditions.
Highlights
Chirality is an important molecular feature that gains particular significance in the case of biologically active compounds since the activity is often dependent from the correct stereochemistry fitting with the target sites in living systems [1,2]
The desymmetrization strategy has attracted great interest [6,7] for the possibility to generate multiple stereocentres starting from relatively simple symmetric prochiral molecules or meso-compounds, without the limitation in the yield connected with the classical kinetic resolution of racemates, that gives at maximum 50% of the desired enantiomer
Among the the different different enzymes used used in in biocatalytic biocatalytic transformations, transformations, lipases lipases are are the the most most popular ones for theirthe wide substrate tolerance, which allows to a notable variety of molecular scaffolds to ones Among wide substrate tolerance, which allows to a notable variety of molecular scaffolds to be different enzymes used in biocatalytic transformations, lipases are the most popular be accommodated and stereoselectively recognized in the enzymatic active site resulting in efficient accommodated andsubstrate stereoselectively in to thea enzymatic active resulting efficient ones for their wide tolerance,recognized which allows notable variety of site molecular scaffolds to be kinetic resolution or desymmetrization processes
Summary
Chirality is an important molecular feature that gains particular significance in the case of biologically active compounds since the activity is often dependent from the correct stereochemistry fitting with the target sites in living systems [1,2]. When a desymmetrization of a substrate A is carried out in the presence of a catalyst with consuming the minor enantiomer of B, which still has the catalyst-matched R-enantiotopic position a given stereopreference, for example R or pro-R, a R-enantioenriched mono-functionalized product intact and suitable to be further transformed If this is the case, the overall process results. Effective desymmetrization protocols synthesis of pharmaceuticals and desymmetrization processes [14,15,16], taking advantages in the have been developed for substrates bearing a variety of functional groups, including all-carbon quaternary stereocentres [13], and identified as key steps in the synthesis of several chiral natural compounds or drugs.
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