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Literature summary for 4.2.1.B20 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

Application Comment Organism
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)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3-deoxyachilleol A Priestia megaterium from squalene (+)-ambrein
-
?
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 ?
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 ?
-
?
squalene + H2O Priestia megaterium
-
8alpha-hydroxypolypoda-13,17,21-triene intermediate product ?

Organism

Organism UniProt Comment Textmining
Priestia megaterium
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-deoxyachilleol A from squalene Priestia megaterium (+)-ambrein
-
?
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 ?
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 ?
-
?
additional information symmetric and asymmetric onoceroids can be biosynthesized by a single enzyme via an intermediate cyclized at one terminus of squalene Priestia megaterium ?
-
?
squalene + H2O
-
Priestia megaterium 8alpha-hydroxypolypoda-13,17,21-triene intermediate product ?

Synonyms

Synonyms Comment Organism
BmeTC
-
Priestia megaterium
onoceroid synthase
-
Priestia megaterium

General Information

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