Biocatalytic asymmetric formation of tetrahydro-β-carbolines

Bernhardt, P, Usera, AR and O'Connor, SE (2010) Biocatalytic asymmetric formation of tetrahydro-β-carbolines. Tetrahedron Letters, 51 (33). pp. 4400-4402.

Full text not available from this repository. (Request a copy)

Abstract

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
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Related URLs:
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 13:53
Last Modified: 25 Jul 2018 04:10
URI: https://ueaeprints.uea.ac.uk/id/eprint/38402
DOI: 10.1016/j.tetlet.2010.06.075

Actions (login required)

View Item