Bioorganic and Medicinal Chemistry p. 1338 - 1346 (2018)
Update date:2022-08-05
Topics:
Herter, Susanne
Medina, Florian
Wagschal, Simon
Benha?m, Cyril
Leipold, Friedemann
Turner, Nicholas J.
A library of 132 racemic chiral amines (α-substituted methylbenzylamines, benzhydrylamines, 1,2,3,4-tetrahydronaphthylamines (THNs), indanylamines, allylic and homoallylic amines, propargyl amines) was screened against the most versatile monoamine oxidase (MAO-N) variants D5, D9 and D11. MAO-N D9 exhibited the highest activity for most substrates and was applied to the deracemisation of a comprehensive set of selected primary amines. In all cases, excellent enantioselectivity was achieved (e.e. >99%) with moderate to good yields (55–80%). Conditions for the deracemisation of primary amines using a MAO-N/borane system were further optimised using THN as a template addressing substrate load, nature of the enzyme preparation, buffer systems, borane sources, and organic co-solvents.
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Doi:10.1021/ol102318k
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