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Literature summary for 4.2.3.130 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
Search for more literature for 4.2.3.130

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Priestia megaterium
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-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-deoxyachilleol A
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 Priestia megaterium (+)-ambrein
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 ?
8alpha-hydroxypolypoda-13,17,21-triene
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 Priestia megaterium onoceranoxide + 14beta-hydroxyonocera-8(26)-ene
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 ?
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
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 ?
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 ?
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 ?
squalene
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 Priestia megaterium 8alpha-hydroxypolypoda-13,17,21-triene
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 ?
tetraprenyl-beta-curcumene + H2O
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 Priestia megaterium baciterpenol A
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 ?

Synonyms

Synonyms Comment Organism
BmeTC
-
 Priestia megaterium
More cf. onoceroid synthase Priestia megaterium
tetraprenyl-beta-curcumene cyclase
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 Priestia megaterium