Reaction: (2E,6E)-farnesyl diphosphate + H2O = (–)-drimenol + diphosphate
For diagram of reaction click here and mechanism click here.
Glossary: (–)-drimenol = drim-7-en-11-ol
Other name(s): PhDS; VoTPS3; farnesyl pyrophosphate:drimenol cyclase; drimenol cyclase; (2E,6E)-farnesyl-diphosphate diphosphohydrolase (drimenol-forming)
Systematic name: (2E,6E)-farnesyl-diphosphate diphospho-lyase [cyclising, (–)-drimenol-forming]
Comments: Isolated from the plants Valeriana officinalis (valerian) and Persicaria hydropiper (water pepper). The enzyme does not act on farnesol or drimenol diphosphate. Using 18-oxygen labelled water 18-oxygen was incorporated suggesting involvement of a stabilised carbocation or an equivalent species.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number:
References:
1. Banthorp, D.V., Brown, J.T. and Morris, G.S. Partial purification of farnesyl pyrophosphate:drimenol cyclase and geranylgerany pyrophosphate:sclareol cyclase, using cell culture as a source of material. Phytochemistry 31 (1992) 3391-3395.
2. Kwon, M., Cochrane, S.A., Vederas, J.C. and Ro, D.K. Molecular cloning and characterization of drimenol synthase from valerian plant (Valeriana officinalis). FEBS Lett. 588 (2014) 4597-4603. [PMID: 25447532]
3. Henquet, M.GL., Prota, N., van der Hooft, J.JJ., Varbanova-Herde, M., Hulzink, R.JM., de Vos, M., Prins, M., de Both, M.TJ., Franssen, M.CR., Bouwmeester, H. and Jongsma, M. Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes. Plant J. 90 (2017) 1052-1063. [PMID: 28258968]