5ojl

Publication Abstract from PubMed

Biocatalytic retrosynthetic analysis of dibenz[c,e]azepines has highlighted the use of imine reductase (IRED) and omega-transaminase (omega-TA) biocatalysts to establish the key stereocentres of these molecules. Several enantiocomplementary IREDs were identified for the synthesis of (R)- and (S)-5-methyl-6,7-dihydro-5H-dibenz[c,e]azepine with excellent enantioselectivity, by reduction of the parent imines. Crystallographic evidence suggests that IREDs may be able to bind one conformer of the imine substrate such that, upon reduction, the major product conformer is generated directly. omega-TA biocatalysts were also successfully employed for the production of enantiopure 1-(2-bromophenyl)ethan-1-amine, thus enabling an orthogonal route for the installation of chirality into dibenz[c,e]azepine framework.

Biocatalytic Routes to Enantiomerically Enriched Dibenz[c,e]azepines.,France SP, Aleku GA, Sharma M, Mangas-Sanchez J, Howard RM, Steflik J, Kumar R, Adams RW, Slabu I, Crook R, Grogan G, Wallace TW, Turner NJ Angew Chem Int Ed Engl. 2017 Dec 4;56(49):15589-15593. doi:, 10.1002/anie.201708453. Epub 2017 Nov 7. PMID:29024400^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.