Reaction participants Show >> << Hide
- Name help_outline pre-α-onocerin Identifier CHEBI:138305 Charge 0 Formula C30H50O2 InChIKeyhelp_outline YOXYJGZFQYXPHZ-AEBUGLRVSA-N SMILEShelp_outline C1C[C@@H](C([C@]2([C@]1([C@H](C(CC2)=C)CC/C=C(/CC/C=C(/CC[C@H]3C(O3)(C)C)\C)\C)C)[H])(C)C)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline α-onocerin Identifier CHEBI:138303 (CAS: 511-01-3) help_outline Charge 0 Formula C30H50O2 InChIKeyhelp_outline GESZMTVZGWZBPW-IHIDZKKCSA-N SMILEShelp_outline C1C[C@@H](C([C@]2([C@]1([C@H](C(CC2)=C)CC[C@H]3C(CC[C@@]4([C@@]3(CC[C@@H](C4(C)C)O)C)[H])=C)C)[H])(C)C)O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:54668 | RHEA:54669 | RHEA:54670 | RHEA:54671 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Onocerin biosynthesis requires two highly dedicated triterpene cyclases in a fern Lycopodium clavatum.
Araki T., Saga Y., Marugami M., Otaka J., Araya H., Saito K., Yamazaki M., Suzuki H., Kushiro T.
Onocerin is known for its unusual structure among triterpenoids, with a symmetrical structure that is formed by cyclizations at the both termini of dioxidosqualene. The nature of the enzyme catalyzing these unusual cyclizations has remained elusive for decades. Here, we report the cloning of genes ... >> More
Onocerin is known for its unusual structure among triterpenoids, with a symmetrical structure that is formed by cyclizations at the both termini of dioxidosqualene. The nature of the enzyme catalyzing these unusual cyclizations has remained elusive for decades. Here, we report the cloning of genes responsible for these reactions; they exhibited unprecedented substrate specificities among oxidosqualene cyclase family members. Two genes, LCC and LCD, were identified from the fern Lycopodium clavatum. Expression in yeast revealed that both were required to produce α-onocerin. LCC, the first dioxidosqualene cyclase, catalyzed the production of a novel intermediate pre-α-onocerin from only dioxidosqualene as a substrate; LCD catalyzed the second half of the cyclization, exclusively from pre-α-onocerin. These results demonstrated that these two most unusual oxidosqualene cyclases were involved in onocerin biosynthesis. << Less
ChemBioChem 17:288-290(2016) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.