Enantioselective Biocatalytic Oxidative Symmetrization of Substituted Pyrrolidines

Sometimes, you have to marvel at what nature can do for you.  I remember a time, when I always sort of jealous of what our Biotransformations group could do.  It was the reason I got diverted into biofuel research.  I wanted to know how to set up a biocatalytic system and I still am impressed with what can be done.  Take, for example, what I intend to talk with you about today. The following paper in Angewandte Chemie, Int. Ed, volume 49, 2010 by Nicholas J. Turner et al, “Enantioselective Biocatalytic Oxidative Symmetrization of Substituted Pyrrolidines”, doi: 10.1002/200906655 describes the application of using monoamine oxidase from Aspergillus niger to desymmetrize symmetric amines.  This type of system uses oxygen as the oxidant.  The enzyme has been direct evolved for broad substrate specificity.

Here is a more specific case applied to something of use.

The ee on that carboxylic acid is pretty phenomenal.

I think it is not hard to see how this discovery might help in the production of the following hepatitis C protease inhibitors.

 

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