Monoamine oxidases cascade

E. O Reilly, C. Iglesias, D. Ghislieri, I. Hopwood, I.L. Galman, R.C. Lloyd, N.I. Turner, A regio-and stereoselective w-transaminase/monoamine oxidase cascade for the synthesis of chiral 2,5-disubstituted pyrrolidines, Angew. Chem. Int. Edit 53 (9) (2014) 2447-2450. 

Monoamine oxidase, tyrosine hydroxylase, and L-amino acid oxidase generate hydrogen peroxide as their reaction product. Hydrogen peroxide is also produced by auto-oxidation of catecholamines in the presence of vitamin C. Moreover, phospholipase A2 (PLA2), cyclooxygenase (COX), and lipoxygenase (LOX), the enzymes associated with arachidonic acid release and the arachidonic acid cascade,... 

The reactions were highly regioselective and only minor side products were formed (4-10% yields) under the established conditions. In addition, this reaction could also be carried out on a 500 mg scale under mild conditions. Recently, Kroutil and co-workers developed a novel chemo-en matic derace-mization reaction, which involves two enantioselective oxidation steps and one non-stereoselective reduction step. This concept combines stereoinversion of one substrate enantiomer with a kinetic resolution to transform a racemic substrate to an optically pure product. By using this method, dera-cemization of benzylisoquinolines rac-39 to berbines (S)-41 via the cascade transformation using monoamine oxidase (MAO), BBE, and morpholine-bo-rane concurrently gave optically pure product [S]-41 (>97% ee, HPLC) in up to 88% isolated yield (Scheme 2.14c). 

E. O Reilly, C. Iglesias, N.. Turner, Monoamine oxidase-w-transaminase cascade for the dera-cemisation and dealkylation of amines, ChemCatChem. 00 (1-4) (2014). 

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