Reaction: all-trans-hexaprenyl diphosphate = macrophomene + diphosphate
For diagram of reaction click here
Glossary: macrophomene = (1S,22R)-tricyclo[20.1.01,22]docosa-2,6,10,14,18-pentaene
Other name(s): MpMS
Systematic name: pentaprenyl-diphosphate diphosphate-lyase [cyclizing, macrophomene-forming]
Comments: Isolated from Macrophomina phaseolina, a pathogenic fungus that causes damping off, seedling blight, collar rot, stem rot, charcoal rot, basal stem rot, and root rot on many plant species. The 22-membered ring in macrophomene represents the largest macrocycle discovered in terpenes so far.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Tao, H., Lauterbach, L., Bian, G., Chen, R., Hou, A., Mori, T., Cheng, S., Hu, B., Lu, L., Mu, X., Li, M., Adachi, N., Kawasaki, M., Moriya, T., Senda, T., Wang, X., Deng, Z., Abe, I., Dickschat, J.S. and Liu, T. Discovery of non-squalene triterpenes. Nature 606 (2022) 414-419. [PMID: 35650436]