Reaction: (–)-cyclopenine = viridicatin + methyl isocyanate
For reaction pathway click here and mechanism click here.
Glossary: (–)-cyclopenine = (3S,3'R)-4-methyl-3'-phenyl-1H-spiro[1,4-benzodiazepine-3,2'-oxirane]-2,5-dione
viridicatin = 3-hydroxy-4-phenyl-1H-quinolin-2-one
Other name(s): asqI (gene name)
Systematic name: (–)-cyclopenine methyl-isocyanate lyase (viridicatin-forming)
Comments: This fungal enzyme catalyses a key reaction in the biosynthesis of quinolone compounds, converting the benzodiazepine structure into a quinolone structure. The enzyme is also active with (–)-4'-methoxycyclopenine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
1. Kishimoto, S., Hara, K., Hashimoto, H., Hirayama, Y., Champagne, P.A., Houk, K.N., Tang, Y. and Watanabe, K. Enzymatic one-step ring contraction for quinolone biosynthesis. Nat. Commun. 9 (2018) 2826. [PMID: 30026518]