4.2.3.141: sclareol synthase
This is an abbreviated version!
For detailed information about sclareol synthase, go to the full flat file.
Reaction
Synonyms
EC 3.1.7.4, sclareol synthase, SsSS
ECTree
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General Information on EC 4.2.3.141 - sclareol synthase
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GENERAL INFORMATION 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
evolution
K4HYB0
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
malfunction
K4HYB0
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
metabolism
K4HYB0
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
physiological function
additional information
physiological function
K4HYB0
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
physiological function
K4HYB0
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
