Biocatalytic asymmetric formation of tetrahydro-β-carbolines

Bernhardt, Peter, Usera, Aimee R. and O'Connor, Sarah E. (2010) Biocatalytic asymmetric formation of tetrahydro-β-carbolines. Tetrahedron Letters, 51 (33). pp. 4400-4402.

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Strictosidine synthase triggers the formation of strictosidine from tryptamine and secologanin, thereby generating a carbon-carbon bond and a new stereogenic center. Strictosidine contains a tetrahydro-ß-carboline moiety - an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals. Stereoselective methods to produce tetrahydro-ß-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-ß-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 towards developing a general biocatalytic strategy to access chiral tetrahydro-ß-carbolines.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 13:53
Last Modified: 10 Mar 2024 00:49
DOI: 10.1016/j.tetlet.2010.06.075

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