Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary extracted from

  • Ueda, D.; Hoshino, T.; Sato, T.
    Cyclization of squalene from both termini Identification of an onoceroid synthase and enzymatic synthesis of ambrein (2013), J. Am. Chem. Soc., 135, 18335-18338 .
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.B20 8alpha-hydroxypolypoda-13,17,21-triene Priestia megaterium
-
 onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.1.B20 squalene Priestia megaterium
-
 8alpha-hydroxypolypoda-13,17,21-triene
-
 ?
4.2.1.B20 tetraprenyl-beta-curcumene + H2O Priestia megaterium
-
 baciterpenol A
-
 ?
4.2.3.130 8alpha-hydroxypolypoda-13,17,21-triene Priestia megaterium
-
 onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.3.130 squalene Priestia megaterium
-
 8alpha-hydroxypolypoda-13,17,21-triene
-
 ?
4.2.3.130 tetraprenyl-beta-curcumene + H2O Priestia megaterium
-
 baciterpenol A
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.B20 Priestia megaterium
-
-
-
4.2.3.130 Priestia megaterium
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.B20 3-deoxyachilleol A
-
 Priestia megaterium (+)-ambrein
-
 ?
4.2.1.B20 8alpha-hydroxypolypoda-13,17,21-triene
-
 Priestia megaterium onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.1.B20 8alpha-hydroxypolypoda-13,17,21-triene the BmeTC-catalyzed reaction of the substrate is initiated by the protonation of a terminal isopropylidene moiety, triggering a series of cyclization events, erminated by the nucleophilic addition of a hydroxyl group or the deprotonation of H-26 at the resulting C-8 carbocation, respectively Priestia megaterium onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.1.B20 additional information onoceroids are synthesized from squalene via an intermediate cyclized from one terminus, such as 8alpha-hydroxypolypoda-13,17,21-triene, by cyclization at both termini. Enzyme BmeTC may have single active site: it starts with the initial cascade leading to the bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene from squalene, then turns molecule 8alpha-hydroxypolypoda-13,17,21-triene outside of the active site cavity, and again uptake 8alpha-hydroxypolypoda-13,17,21-triene to catalyze the formation of additional bicyclic and tricyclic structures of onoceranoxide and 14beta-hydroxyonocera-8(26)-ene on the other side of 8alpha-hydroxypolypoda-13,17,21-triene. BmeTC is not only a bifunctional terpene cyclase which converts tetraprenyl-beta-curcumene and squalene into baciterpenol A and 8alpha-hydroxypolypoda-13,17,21-triene but also an onoceroid synthase that catalyzes the convertion of 8alpha-hydroxypolypoda-13,17,21-triene into onoceranoxide and 14beta-hydroxyonocera-8(26)-ene. GC-MS product analysis, overview Priestia megaterium ?
-
 ?
4.2.1.B20 squalene
-
 Priestia megaterium 8alpha-hydroxypolypoda-13,17,21-triene
-
 ?
4.2.1.B20 tetraprenyl-beta-curcumene + H2O
-
 Priestia megaterium baciterpenol A
-
 ?
4.2.3.130 3-deoxyachilleol A
-
 Priestia megaterium (+)-ambrein
-
 ?
4.2.3.130 8alpha-hydroxypolypoda-13,17,21-triene
-
 Priestia megaterium onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.3.130 8alpha-hydroxypolypoda-13,17,21-triene the BmeTC-catalyzed reaction of the substrate is initiated by the protonation of a terminal isopropylidene moiety, triggering a series of cyclization events, erminated by the nucleophilic addition of a hydroxyl group or the deprotonation of H-26 at the resulting C-8 carbocation, respectively Priestia megaterium onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
-
 ?
4.2.3.130 additional information onoceroids are synthesized from squalene via an intermediate cyclized from one terminus, such as 8alpha-hydroxypolypoda-13,17,21-triene, by cyclization at both termini. Enzyme BmeTC may have single active site: it starts with the initial cascade leading to the bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene from squalene, then turns molecule 8alpha-hydroxypolypoda-13,17,21-triene outside of the active site cavity, and again uptake 8alpha-hydroxypolypoda-13,17,21-triene to catalyze the formation of additional bicyclic and tricyclic structures of onoceranoxide and 14beta-hydroxyonocera-8(26)-ene on the other side of 8alpha-hydroxypolypoda-13,17,21-triene. BmeTC is not only a bifunctional terpene cyclase which converts tetraprenyl-beta-curcumene and squalene into baciterpenol A and 8alpha-hydroxypolypoda-13,17,21-triene but also an onoceroid synthase that catalyzes the convertion of 8alpha-hydroxypolypoda-13,17,21-triene into onoceranoxide and 14beta-hydroxyonocera-8(26)-ene. GC-MS product analysis, overview Priestia megaterium ?
-
 ?
4.2.3.130 squalene
-
 Priestia megaterium 8alpha-hydroxypolypoda-13,17,21-triene
-
 ?
4.2.3.130 tetraprenyl-beta-curcumene + H2O
-
 Priestia megaterium baciterpenol A
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.B20 BmeTC
-
 Priestia megaterium
4.2.1.B20 More cf. tetraprenyl-beta-curcumene cyclase, EC 4.2.1.129 Priestia megaterium
4.2.3.130 BmeTC
-
 Priestia megaterium
4.2.3.130 More cf. onoceroid synthase Priestia megaterium
4.2.3.130 tetraprenyl-beta-curcumene cyclase
-
 Priestia megaterium