Biocatalytic asymmetric formation of tetrahydro-β-carbolines

P Bernhardt, AR Usera, SE O'Connor

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)4400-4402
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number33
DOIs
Publication statusPublished - 18 Aug 2010

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