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Biocatalytic asymmetric formation of tetrahydro-?-carbolines.

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-?-carboline moiety - an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals. Stereoselective methods to produce tetrahydro-?-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-?-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-?-carbolines.

SUBMITTER: Bernhardt P

PROVIDER: S-EPMC2913883 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Biocatalytic asymmetric formation of tetrahydro-β-carbolines.

Bernhardt Peter P Usera Aimee R AR O'Connor Sarah E SE

Tetrahedron letters 20100801 33

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-β-carboline moiety - an important N-heterocyclic framework found in a range of natural products and synthetic pharmaceuticals. Stereoselective methods to produce tetrahydro-β-carboline enantiomers are greatly valued. We report that strictosidine synthase from Ophiorrhiza pumila utilizes a range of ...[more]

PMID: 20689670

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