KEGG   ORTHOLOGY: K18113
Entry
K18113            Tight     KO                                     
Symbol
MDS
Name
miltiradiene synthase / copalyl diphosphate synthase [EC:4.2.3.131 5.5.1.12]
Pathway
map00904  Diterpenoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Reaction
R06298  (+)-copalyl-diphosphate lyase (decyclizing)
R10585  (+)-copaly-diphosphate diphosphate-lyase (cyclizing, miltiradiene-forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K18113  MDS; miltiradiene synthase / copalyl diphosphate synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.131  miltiradiene synthase
     K18113  MDS; miltiradiene synthase / copalyl diphosphate synthase
 5. Isomerases
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.12  copalyl diphosphate synthase
     K18113  MDS; miltiradiene synthase / copalyl diphosphate synthase
Other DBs
GO: 0050559
Genes
SMO: SELMODRAFT_450918
Reference
PMID:22027823
  Authors
Sugai Y, Ueno Y, Hayashi K, Oogami S, Toyomasu T, Matsumoto S, Natsume M, Nozaki H, Kawaide H
  Title
Enzymatic (13)C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii.
  Journal
J Biol Chem 286:42840-7 (2011)
DOI:10.1074/jbc.M111.302703
  Sequence
[smo:SELMODRAFT_450918]
LinkDB

KEGG   ENZYME: 4.2.3.131
Entry
EC 4.2.3.131                Enzyme                                 
Name
miltiradiene synthase;
SmMDS;
SmiKSL;
RoKSL
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
Sysname
(+)-copalyl-diphosphate diphosphate-lyase (cyclizing, miltiradiene-forming)
Reaction(IUBMB)
(+)-copalyl diphosphate = miltiradiene + diphosphate [RN:R10585]
Reaction(KEGG)
R10585
Substrate
(+)-copalyl diphosphate [CPD:C11901]
Product
miltiradiene [CPD:C20711];
diphosphate [CPD:C00013]
Comment
Isolated from the plants Rosmarinus officinalis (rosemary) and Salvia miltiorrhiza. The enzyme from the plant Selaginella moellendorffii is mutifunctional and also catalyses EC 5.5.1.12, copalyl diphosphate synthase [2].
History
EC 4.2.3.131 created 2012
Pathway
ec00904  Diterpenoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K18113  miltiradiene synthase / copalyl diphosphate synthase
Genes
SMO: SELMODRAFT_450918
Reference
1  [PMID:19905026]
  Authors
Gao W, Hillwig ML, Huang L, Cui G, Wang X, Kong J, Yang B, Peters RJ
  Title
A functional genomics approach to tanshinone biosynthesis provides stereochemical insights.
  Journal
Org Lett 11:5170-3 (2009)
DOI:10.1021/ol902051v
Reference
2  [PMID:22027823]
  Authors
Sugai Y, Ueno Y, Hayashi K, Oogami S, Toyomasu T, Matsumoto S, Natsume M, Nozaki H, Kawaide H
  Title
Enzymatic (13)C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii.
  Journal
J Biol Chem 286:42840-7 (2011)
DOI:10.1074/jbc.M111.302703
  Sequence
[smo:SELMODRAFT_450918]
Reference
3  [PMID:24569175]
  Authors
Bruckner K, Bozic D, Manzano D, Papaefthimiou D, Pateraki I, Scheler U, Ferrer A, de Vos RC, Kanellis AK, Tissier A
  Title
Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes.
  Journal
Phytochemistry 101:52-64 (2014)
DOI:10.1016/j.phytochem.2014.01.021
Other DBs
ExplorEnz - The Enzyme Database: 4.2.3.131
IUBMB Enzyme Nomenclature: 4.2.3.131
ExPASy - ENZYME nomenclature database: 4.2.3.131
BRENDA, the Enzyme Database: 4.2.3.131
LinkDB

KEGG   REACTION: R10585
Entry
R10585                      Reaction                               
Name
(+)-copaly-diphosphate diphosphate-lyase (cyclizing, miltiradiene-forming)
Definition
Copalyl diphosphate <=> Miltiradiene + Diphosphate
Equation
C11901 <=> C20711 + C00013
Reaction class
RC03205  C11901_C20711
Enzyme
4.2.3.131
Pathway
rn00904  Diterpenoid biosynthesis
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 4. Lyase reactions
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.131
     R10585  Copalyl diphosphate <=> Miltiradiene + Diphosphate
Orthology
K18113  miltiradiene synthase / copalyl diphosphate synthase [EC:4.2.3.131 5.5.1.12]
Other DBs
RHEA: 33986
LinkDB

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