Biocatalytic asymmetric formation of tetrahydro-beta-carbolines

Bernhardt, Peter; Usera, Aimee R.; O'Connor, Sarah E.

doi:10.1016/j.tetlet.2010.06.075

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Biocatalytic asymmetric formation of tetrahydro-beta-carbolines

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Bernhardt, P., Usera, A. R., & O'Connor, S. E. (2010). Biocatalytic asymmetric formation of tetrahydro-beta-carbolines. Tetrahedron Letters, 51(33), 4400-4402. doi:10.1016/j.tetlet.2010.06.075.

Cite as: https://hdl.handle.net/21.11116/0000-0002-AEA7-E

Abstract

Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-catbon bond and a new stereogenic center Strictosidine contains a tetrahydro-beta-carboline moiety an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals Stereoselective methods to produce tetrahydro-B-carboline enantiomers are greatly valued We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of simple achiral aldehydes and substituted tryptamines to form highly enantioenriched (ee >98%) tetrahydro-beta-carbolines via a Pictet-Spengler reaction This is the first example of aldehyde substrate promiscuity in the strictosidine synthase family of enzymes and represents a first step toward developing a general biocatalytic strategy to access chiral tetrahydro-beta-carbolines (C) 2010 Elsevier Ltd All rights reserved