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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

Application

EC Number Application Comment Organism
4.2.1.B20 synthesis the onoceroid synthase function of BmeTC enables the synthesis of (+)-ambrein, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase-catalyzed reaction from easily available squalene Priestia megaterium

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.B20 3-deoxyachilleol A Priestia megaterium from squalene (+)-ambrein
-
?
4.2.1.B20 8alpha-hydroxypolypoda-13,17,21-triene Priestia megaterium the enzyme constructs the 6/6/6/6-tetracyclic scaffold baciterpenol A from the head-to-tail monocyclic tetraprenyl-betacurcumene as sesquarterpene cyclase, EC 4.2.1.137, and it also forms the 6/6/7/6/6-pentacyclic onoceranoxide and the 6/6 + 6/6-tetracyclic (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl]decahydron from the tail-to-tail acyclic triterpene squalene via the 6/6-bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene onoceranoxide + ((1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl}decahydronaphthalen-2-ol ratio 64:36 ?
4.2.1.B20 additional information Priestia megaterium tetraprenyl-beta-curcumene cyclase from Bacillus megaterium is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail tetraprenyl-beta-curcumene and tail-to-tail squalene into pentacyclic and bicyclic products, respectively, in vivo. BmeTC has an unprecedented catalytic function in cyclizing squalene from both termini and is an onoceroid synthase. The function of BmeTC enables the synthesis of (+)-ambrein ?
-
?
4.2.1.B20 squalene + H2O Priestia megaterium
-
8alpha-hydroxypolypoda-13,17,21-triene intermediate product ?

Organism

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.B20 3-deoxyachilleol A from squalene Priestia megaterium (+)-ambrein
-
?
4.2.1.B20 8alpha-hydroxypolypoda-13,17,21-triene the enzyme constructs the 6/6/6/6-tetracyclic scaffold baciterpenol A from the head-to-tail monocyclic tetraprenyl-betacurcumene as sesquarterpene cyclase, EC 4.2.1.137, and it also forms the 6/6/7/6/6-pentacyclic onoceranoxide and the 6/6 + 6/6-tetracyclic (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl]decahydron from the tail-to-tail acyclic triterpene squalene via the 6/6-bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene Priestia megaterium onoceranoxide + ((1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl}decahydronaphthalen-2-ol ratio 64:36 ?
4.2.1.B20 additional information tetraprenyl-beta-curcumene cyclase from Bacillus megaterium is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail tetraprenyl-beta-curcumene and tail-to-tail squalene into pentacyclic and bicyclic products, respectively, in vivo. BmeTC has an unprecedented catalytic function in cyclizing squalene from both termini and is an onoceroid synthase. The function of BmeTC enables the synthesis of (+)-ambrein Priestia megaterium ?
-
?
4.2.1.B20 additional information symmetric and asymmetric onoceroids can be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene Priestia megaterium ?
-
?
4.2.1.B20 squalene + H2O
-
Priestia megaterium 8alpha-hydroxypolypoda-13,17,21-triene intermediate product ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.B20 BmeTC
-
Priestia megaterium
4.2.1.B20 onoceroid synthase
-
Priestia megaterium

General Information

EC Number General Information Comment Organism
4.2.1.B20 metabolism onoceroids are triterpenoids biosynthesized from squalene or (3S)-2,3-oxidosqualene by cyclization from both termini Priestia megaterium