1. Biosynthesis of Shearinine: Diversification of a Tandem Prenyl Moiety of Fungal Indole Diterpenes.
- Author
-
Liu C, Minami A, Dairi T, Gomi K, Scott B, and Oikawa H
- Subjects
- Aspergillus oryzae enzymology, Aspergillus oryzae genetics, Biosynthetic Pathways, Cyclization, Fungal Proteins genetics, Fungal Proteins metabolism, Hydroxylation, Indole Alkaloids chemistry, Molecular Structure, Oxidation-Reduction, Prenylation, Aspergillus oryzae metabolism, Diterpenes metabolism, Genes, Fungal, Indole Alkaloids metabolism, Indoles metabolism
- Abstract
The late-stage biosynthetic pathway of the indole diterpene shearinine involving four enzymatic reactions (JanQDOJ) was elucidated by an efficient heterologous expression system using Aspergillus oryzae. Key oxidative cyclization, forming a characteristic A/B bicyclic shearinine core by flavoprotein oxidase, was studied using a substrate analogue and a buffer containing H
2 18 O. These experimental data provided evidence that JanO catalyzes two-step oxidation via a hydroxylated product and that the JanO reaction involves the hydride-transfer mechanism.- Published
- 2016
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