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Literature summary extracted from

  • Schulte, S.; Potter, K.C.; Lemke, C.; Peters, R.J.
    Catalytic bases and stereocontrol in Lamiaceae class II diterpene cyclases (2018), Biochemistry, 57, 3473-3479 .
    View publication on PubMedView publication on EuropePMC

Protein Variants

EC Number Protein Variants Comment Organism
5.5.1.12 H315N/T316V site-directed mutagenesis, the double mutant produces terpentedienyl diphosphate, which is derived from complete substituent rearrangement of syn rather than normal labdaenyl intermediate. Alteration of the residues that normally serve as the catalytic base can impact stereocontrol Salvia miltiorrhiza

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.5.1.12 geranylgeranyl diphosphate Salvia miltiorrhiza
-
 (+)-copalyl diphosphate
-
 r

Organism

EC Number Organism UniProt Comment Textmining
5.5.1.12 Salvia miltiorrhiza B8PQ84
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.5.1.12 geranylgeranyl diphosphate
-
 Salvia miltiorrhiza (+)-copalyl diphosphate
-
 r

Synonyms

EC Number Synonyms Comment Organism
5.5.1.12 CPP synthase
-
 Salvia miltiorrhiza
5.5.1.12 SmCPS
-
 Salvia miltiorrhiza

General Information

EC Number General Information Comment Organism
5.5.1.12 evolution the enzyme is a class II diterpene cyclase Salvia miltiorrhiza
5.5.1.12 malfunction changing two adjacent residues that seem to serve as the catalytic base in the normal CPP synthase from Salvia miltiorrhiza (SmCPS) to the residues found in the closely related perigrinol diphosphate synthase from Marrubium vulgare (MvPPS), which produces a partially rearranged and hydroxylated product derived from the distinct syn stereoisomer of labdaenyl intermediate, alters the product outcome, cf. EC 5.5.1.14. Specifically, the relevant SmCPS:H315N/T316V double mutant produces terpentedienyl diphosphate, which is derived from complete substituent rearrangement of syn rather than normal labdaenyl intermediate. Alteration of the residues that normally serve as the catalytic base can impact stereocontrol Salvia miltiorrhiza
5.5.1.12 additional information class II diterpene cyclases (DTCs) utilize a general acid-base catalyzed cyclo-isomerization reaction to produce various stereoisomers of the eponymous labdaenyl carbocation intermediate, which can then undergo rearrangement and/or the addition of water prior to terminating deprotonation. Identification of the pair of residues that cooperatively serves as the catalytic base in the DTCs producing ent-copalyl diphosphate (CPP) required for gibberellin phytohormone biosynthesis in all vascular plants, overview Salvia miltiorrhiza