Reaction participants Show >> << Hide
- Name help_outline (S)-2,3-epoxysqualene Identifier CHEBI:15441 Charge 0 Formula C30H50O InChIKeyhelp_outline QYIMSPSDBYKPPY-RSKUXYSASA-N SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C 2D coordinates Mol file for the small molecule Search links Involved in 29 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline baruol Identifier CHEBI:63712 Charge 0 Formula C30H50O InChIKeyhelp_outline XJJAVFWIAXATMT-KNUFMLCHSA-N SMILEShelp_outline [H][C@@]12CC[C@H](O)C(C)(C)C1=CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)C[C@](C)(CCC=C(C)C)CC[C@]12C 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:31987 | RHEA:31988 | RHEA:31989 | RHEA:31990 | |
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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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An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis.
Lodeiro S., Xiong Q., Wilson W.K., Kolesnikova M.D., Onak C.S., Matsuda S.P.T.
The genome of the model plant Arabidopsis thaliana encodes 13 oxidosqualene cyclases, 9 of which have been characterized by heterologous expression in yeast. Here we describe another cyclase, baruol synthase (BARS1), which makes baruol (90%) and 22 minor products (0.02-3% each). This represents as ... >> More
The genome of the model plant Arabidopsis thaliana encodes 13 oxidosqualene cyclases, 9 of which have been characterized by heterologous expression in yeast. Here we describe another cyclase, baruol synthase (BARS1), which makes baruol (90%) and 22 minor products (0.02-3% each). This represents as many triterpenes as have been reported for all other Arabidopsis cyclases combined. By accessing an extraordinary repertoire of mechanistic pathways, BARS1 makes numerous skeletal types and deprotonates the carbocation intermediates at 14 different sites around rings A, B, C, D, and E. This undercurrent of structural and mechanistic diversity in a superficially accurate enzyme is incompatible with prevailing concepts of triterpene biosynthesis, which posit tight control over the mechanistic pathway through cation-pi interactions, with a single proton acceptor in a hydrophobic active site. Our findings suggest that mechanistic diversity is the default for triterpene biosynthesis and that product accuracy results from exclusion of alternative pathways. << Less
J. Am. Chem. Soc. 129:11213-11222(2007) [PubMed] [EuropePMC]
Comments
Published in : Nunez, M.J., Lopez, M.R., Jimenez, I.A., Moujir, L.M., Ravelo, A.G., Bazzocchi, I.L. "First examples of tetracyclic triterpenoids with a D:B-friedobaccharane skeleton. A tentative biosynthetic route." Tetrahedron Letters. 45:7367-7370,2004.