Nodulisporic acid E biosynthesis: in vivo characterisation of NodD1, an indole-diterpene prenyltransferase that acts on an emindole SB derived indole-diterpene scaffold

Abstract

Prenylation of aromatic compounds is a key tailoring reaction in biosynthesis of bioactive indole-diterpenes.

Biosynthesis of indole diterpenes: a reconstitution approach in a heterologous host

“…30 In addition, functional JanD/JanO orthologs NodD1/NodO were found, strongly suggesting that the characteristic bicyclic system of dihydroNA-D ( 42 ) via 41 is likely synthesized in a similar transformation. 52,56…”

Synthesis of rearranged indole diterpenes of the paxilline type

“…1). 13,42–44 Complex indole moieties that arise from multiple prenylations of the aromatic ring and subsequent oxidation events feature prominently in many other indole diterpenes, including penitrem A ( 3 ), lolitrem B ( 4 ), and shearinine A ( 5 , see Fig. 1).…”

Biosynthesis of Nodulisporic Acids: A Multifunctional Monooxygenase Delivers a Complex and Highly Branched Array

“…The P450 monooxygenase NodW was subsequently found to install the carboxylic acid functionality characteristic of the nodulisporic acids, while the prenyl transferase NodD1 diprenylated the indole giving rise to nodulisporic acid E (NAE), laying the foundation for the complex ring systems observed in NAA (Scheme 1). [8a, 9] …”

“…These genes were predicted to encode three P450 monooxygenases (NodR, Z, and J), two paralogous FAD‐dependent monooxygenases (NodY1 and Y2), an FAD‐dependent cyclo‐oxidase (NodO), a second aromatic prenyl transferase (NodD2), and an acetyl‐CoA transferase (NodX) (Figure 2). [8a, 9] …”