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Literature summary extracted from

  • Hallahan, T.W.; Croteau, R.
    Monoterpene biosynthesis: mechanism and stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (+)-cis- and (+)-trans-sabinene hydrate (1989), Arch. Biochem. Biophys., 269, 313-326.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.3.11 (RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide
-
 Origanum majorana
4.2.3.11 (RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate
-
 Origanum majorana
4.2.3.11 6,7-dihydrogeranyl diphosphate competitive Origanum majorana

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.3.11 0.001
-
 (3S)-linalyl diphosphate pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0019
-
 geranyl diphosphate pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0027
-
 (3R)-linalyl diphosphate pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0045
-
 6,7-dihydrogeranyl diphosphate pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0105
-
 neryl diphosphate pH 7.0, 30°C Origanum majorana

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.11 Mg2+ absolute requirement for divalent cation in the reaction with 6,7-dihydrogeranyl diphosphate, preference for Mn2+ over Mg2+ Origanum majorana
4.2.3.11 Mn2+ absolute requirement for divalent cation in the reaction with 6,7-dihydrogeranyl diphosphate, preference for Mn2+ over Mg2+ Origanum majorana

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.11 Origanum majorana
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.3.11 partial Origanum majorana

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.11 geranyl diphosphate + H2O = sabinene hydrate + diphosphate both cis- and trans-isomers of sabinene hydrate are formed. (3R)-Linalyl diphosphate is an intermediate in the reaction, mechanism and stereochemistry Origanum majorana
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.3.11 leaf
-
 Origanum majorana
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.11 (3R)-linalyl diphosphate + H2O
-
 Origanum majorana (1S,2S,4R)-(E)-sabinene hydrate + diphosphate
-
 ?
4.2.3.11 (3S)-linalyl diphosphate
-
 Origanum majorana (1R,2R,4S)-(E)-sabinene hydrate + diphosphate
-
 ?
4.2.3.11 2,3-methanogeranyl diphosphate + H2O at 1.5% of the rate of conversion of geranyl diphosphate to sabinene hydrate, noncyclizable substrate analog of geranyl diphosphate Origanum majorana ?
-
 ?
4.2.3.11 6,7-dihydrogeranyl diphosphate + H2O noncyclizable substrate analog of geranyl diphosphate Origanum majorana 6,7-dihydromyrcene + ?
-
 ?
4.2.3.11 geranyl diphosphate
-
 Origanum majorana sabinene hydrate + diphosphate the configuration at c1 of geranyl diphosphate is retained in the enzymatic conversion to (+)-cis and (+)-trans-sabinene hydrate ?
4.2.3.11 geranyl diphosphate
-
 Origanum majorana sabinene hydrate + diphosphate both cis- and trans-isomers of sabinene hydrate are formed ?
4.2.3.11 linalyl diphosphate 3R- and 3S-configuration Origanum majorana sabinene hydrate + diphosphate cis- and trans-sabinene hydrate ?
4.2.3.11 neryl diphosphate
-
 Origanum majorana sabinene hydrate + diphosphate
-
 ?

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.2.3.11 0.0003
-
 (RS)-methyl-(4-methylpent-3-en-1-yl)vinyl sulfonium perchlorate pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0028
-
 (RS)-dimethyl-(4-methylcyclohex-3-en-1-yl)sulfonium iodide pH 7.0, 30°C Origanum majorana
4.2.3.11 0.0042
-
 6,7-dihydrogeranyl diphosphate pH 7.0, 30°C Origanum majorana