asperlicin C + NAD(P)H + H+ + O2 = asperlicin E + NAD(P)+ + H2O
asperlicin C,NAD(P)H:oxygen oxidoreductase
The enzyme, characterized from the fungus Aspergillus alliaceus, contains an FAD cofactor. The enzyme inserts a hydroxyl group, leading to formation of a N-C bond that creates an additional cycle between the bicyclic indole and the tetracyclic core moieties, resulting in the heptacyclic asperlicin E.
Haynes, S.W., Gao, X., Tang, Y. and Walsh, C.T. Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: a two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E. J. Am. Chem. Soc.134 (2012) 17444–17447. [DOI] [PMID: 23030663]