Enzymes
UniProtKB help_outline | 1 proteins |
Enzyme class help_outline |
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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 α-seco-amyrin Identifier CHEBI:63464 Charge 0 Formula C30H50O InChIKeyhelp_outline BMTRRCREWLAQBX-CHJNBIAGSA-N SMILEShelp_outline [H][C@]1(CCC2=C(C)CC[C@@]3(C)CC[C@@H](C)[C@H](C)[C@@]23[H])C(C)=CC[C@@]2([H])C(C)(C)[C@@H](O)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:31871 | RHEA:31872 | RHEA:31873 | RHEA:31874 | |
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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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Origin of structural diversity in natural triterpenes: direct synthesis of seco-triterpene skeletons by oxidosqualene cyclase.
Shibuya M., Xiang T., Katsube Y., Otsuka M., Zhang H., Ebizuka Y.
At1g78500, one of the oxidosqualene cyclase (OSC) homologues from Arabidopsis thaliana, was expressed in a lanosterol synthase-deficient yeast strain and the products were analyzed. In addition to the known triterpenes, this OSC was found to produce two new triterpenes, the structures of which wer ... >> More
At1g78500, one of the oxidosqualene cyclase (OSC) homologues from Arabidopsis thaliana, was expressed in a lanosterol synthase-deficient yeast strain and the products were analyzed. In addition to the known triterpenes, this OSC was found to produce two new triterpenes, the structures of which were determined by NMR and MS analyses. The new triterpenes are C-ring-seco-beta-amyrin (1) and C-ring-seco-alpha-amyrin (2) and named beta-seco-amyrin and alpha-seco-amyrin, respectively. beta-seco-Amyrin is produced from the oleanyl cation through bond cleavage between C8 and C14, and alpha-seco-amyrin is produced from the ursanyl cation in the same manner. Together with Grob fragmentation catalyzed by another OSC (marneral synthase) from A. thaliana, the formation of seco-amyrins by this OSC revealed that OSCs not only catalyze carbon-carbon bond formations and Wagner-Meerwein rearrangements but also cleave preformed ring systems in cationic intermediates. Based on this information, direct production of other natural seco-triterpenes by OSCs is proposed. << Less
J. Am. Chem. Soc. 129:1450-1455(2007) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.