EC Number   |
General Information |
Reference |
|---|
  4.2.3.141 | evolution |
in angiosperms, class II diTPSs that enable water quenching of the labda-13-en-8-yl carbocation are found in six different plant families, phylogenetic tree, overview |
749408 |
| 4.2.3.141 | malfunction |
mutants N431D and N431Q selectively produce (13S)-sclareol, with SsSS:N431Q exhibiting almost complete reversal of the stereoselective addition of water, i.e., while wild-type SsSS produces (13R)-sclareol in 80% enantiomeric excess (ee), SsSS:N431Q produces 70% ee of (13S)-sclareol. The single residue change N431Q essentially flips the stereochemical outcome, changing the addition of water to the si face of the double bond in (13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate providing biosynthetic access to (13S)-sclareol |
746584 |
| 4.2.3.141 | metabolism |
the enzyme substrate is derived from bicyclization of the general diterpene precursor (E,E,E)-geranylgeranyl diphosphate (GGPP) by class II diterpene cyclase copal-8-ol diphosphate hydratase, EC 4.2.1.133 |
746584 |
| 4.2.3.141 | more |
homology modeling |
746584 |
| 4.2.3.141 | physiological function |
enzymes labda-13-en-8-ol diphosphate synthase and sclareol synthase are two monofunctional diterpene synthases which, together, produce the diterpenoid specialized metabolite sclareol in a two-step process. Labda-13-en-8-ol diphosphate synthase produces labda-13-en-8-ol diphosphate as major product from geranylgeranyl diphosphate with some minor quantities of its non-hydroxylated analogue, (9 S, 10 S)-copalyl diphosphate. Sclareol synthase then transformes these intermediates into sclareol and manool, respectively |
719185 |
| 4.2.3.141 | physiological function |
in nature, diterpene synthase (diTPS) enzymes are essential for generating diverse diterpene hydrocarbon scaffolds. Major commercial diterpenoids include sclareol from clary sage (Salvia sclarea) used as a precursor for ambroxide fragrance and fixatives in perfume manufacture. In angiosperms, class II diTPSs that enable water quenching of the labda-13-en-8-yl carbocation are found in six different plant families, these class II diTPSs can pair with class I enzymes, converting oxygenated prenyl diphosphates through ionization with or without secondary cyclization or additional hydroxylation to afford diterpene alcohols, including manoyl oxide, sclareol and cis-abienol, that are of interest in the fragrance industry |
749408 |
