Prikl Biokhim Mikrobiol. 1992 Nov-Dec;28(6):844-57.

[Biosynthesis of ergot alkaloids. Some new results on an old problem (Review)].

[Article in Russian]

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Department of Chemistry BG-10, University of Washington, Seattle.

Abstract

The biosynthetic pathway leading from L-tryptophan, mevalonic acid and methionine to the tetracyclic ergoline ring system of the ergot alkaloids in Claviceps species is reviewed. This pathway entails many mechanistically intriguing features. Recent studies are also discussed which reveal the stereochemical course of the isoprenylation of tryptophan and of the N-methylation of dimethylallyltryptophan (DMAT) and which shed some light on the likely steps leading from the open-chain precursors, N-methyl-DMAT to the tricyclic intermediate, chanoclavine-1. Finally, some plans are outlined to probe the evolutionary relationship of ergot alkaloid biosynthesis in fungi to that in higher plants of the family Convolvulaceae.

PMID:: 1494571; [PubMed - indexed for MEDLINE]

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Alkaloid cluster gene ccsA of the ergot fungus Claviceps purpurea encodes chanoclavine I synthase, a flavin adenine dinucleotide-containing oxidoreductase mediating the transformation of N-methyl-dimethylallyltryptophan to chanoclavine I. [Appl Environ Microbiol. 2010]
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