Reaction participants Show >> << Hide
- Name help_outline aculene D Identifier CHEBI:155910 Charge 0 Formula C14H20O2 InChIKeyhelp_outline IIQOUDJDCRTCJY-MBNYWOFBSA-N SMILEShelp_outline [C@H]1([C@]2([C@](CC=C(C1)C)(C(=CC2=O)CC)[H])C)O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
L-prolyl-[peptidyl-carrier protein]
Identifier
RHEA-COMP:14109
Reactive part
help_outline
- Name help_outline O-(S-L-prolylpantetheine-4'-phosphoryl)serine residue betaine Identifier CHEBI:138622 Charge 0 Formula C19H33N4O9PS SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CSC([C@@H]1CCC[NH2+]1)=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline aculene B Identifier CHEBI:155913 Charge 1 Formula C19H28NO3 InChIKeyhelp_outline DLPUOZGNMZKXKB-YEWFCNIMSA-O SMILEShelp_outline [C@H]1([C@]2([C@](CC=C(C1)C)(C(=CC2=O)CC)[H])C)OC([C@H]3[NH2+]CCC3)=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
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Namehelp_outline
holo-[peptidyl-carrier protein]
Identifier
RHEA-COMP:11480
Reactive part
help_outline
- Name help_outline O-(pantetheine-4ʼ-phosphoryl)-L-serine residue Identifier CHEBI:64479 Charge -1 Formula C14H25N3O8PS SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CS 2D coordinates Mol file for the small molecule Search links Involved in 207 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:65104 | RHEA:65105 | RHEA:65106 | RHEA:65107 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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The biosynthesis of norsesquiterpene aculenes requires three cytochrome P450 enzymes to catalyze a stepwise demethylation process.
Lee C.F., Chen L.X., Chiang C.Y., Lai C.Y., Lin H.C.
Aculenes are a unique class of norsequiterpenes (C<sub>14</sub> ) that are produced by Aspergillus aculeatus. The nordaucane skeleton in aculenes A-D may be derived from an ent-daucane precursor through demethylation, however, the enzymes involved remain unexplored. We identified the biosynthetic ... >> More
Aculenes are a unique class of norsequiterpenes (C<sub>14</sub> ) that are produced by Aspergillus aculeatus. The nordaucane skeleton in aculenes A-D may be derived from an ent-daucane precursor through demethylation, however, the enzymes involved remain unexplored. We identified the biosynthetic gene cluster and characterized the biosynthetic pathway based on gene inactivation, feeding experiments, and heterologous reconstitution in Saccharomyces cerevisiae and Aspergillus oryzae. We discovered that three cytochrome P450 monoxygenases are required to catalyze the stepwise demethylation process. AneF converts the 12-methyl group into a carboxylic acid and AneD installs the 10-hydroxy group for later tautomerization and stabilization. Finally, AneG installs an electron-withdrawing carbonyl group at the C-2 position, which triggers C-12 decarboxylation to yield the nordaucane skeleton. Additionally, a terpene cyclase (AneC) was found that forms a new product (dauca-4,7-diene). << Less
Angew. Chem. Int. Ed. 58:18414-18418(2019) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.