Reaction participants Show >> << Hide
- Name help_outline protoaustinoid A Identifier CHEBI:156350 Charge 0 Formula C26H38O5 InChIKeyhelp_outline RYGSIWHMOJZNHQ-LXDQHLFBSA-N SMILEShelp_outline [C@@]12([C@@]3([C@]([C@]4([C@](CC3)(C([C@@H](CC4)O)(C)C)[H])C)(C[C@](C1=C)(C(=O)[C@H](C2=O)C)C)[H])C)C(=O)OC 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 A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,883 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline protoaustinoid B Identifier CHEBI:156380 Charge 0 Formula C26H36O5 InChIKeyhelp_outline GHUUUTISLYNCMY-SGMCZAPESA-N SMILEShelp_outline [C@@]12([C@@]3([C@]([C@]4([C@](CC3)(C(C(CC4)=O)(C)C)[H])C)(C[C@](C1=C)(C(=O)[C@H](C2=O)C)C)[H])C)C(=O)OC 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 AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,812 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:65176 | RHEA:65177 | RHEA:65178 | RHEA:65179 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Publications
-
Discovery of key dioxygenases that diverged the paraherquonin and acetoxydehydroaustin pathways in Penicillium brasilianum.
Matsuda Y., Iwabuchi T., Fujimoto T., Awakawa T., Nakashima Y., Mori T., Zhang H., Hayashi F., Abe I.
Paraherquonin (1), a fungal meroterpenoid produced by Penicillium brasilianum NBRC 6234, possesses a unique, highly congested hexacyclic molecular architecture. Here we identified the biosynthetic gene cluster of 1 (the prh cluster) and elucidated the pathway up to berkeleydione (2), which serves ... >> More
Paraherquonin (1), a fungal meroterpenoid produced by Penicillium brasilianum NBRC 6234, possesses a unique, highly congested hexacyclic molecular architecture. Here we identified the biosynthetic gene cluster of 1 (the prh cluster) and elucidated the pathway up to berkeleydione (2), which serves as the key intermediate for the biosynthesis of 1 as well as many other meroterpenoids. Interestingly, the nonheme iron and α-ketoglutarate-dependent dioxygenase PrhA constructs the cycloheptadiene moiety to afford 2 from preaustinoid A1 (6), probably via the homoallyl-homoallyl radical rearrangement. Additionally, another fungal strain, P. brasilianum MG11, which produces acetoxydehydroaustin instead of 1, was found to have a gene cluster nearly identical to the prh cluster. The dioxygenase encoded by the cluster shares 92% sequence identity with PrhA, and also accepts 6 but produces preaustinoid A3 (17) with a spiro-lactone system, generating a diverging point for the two different meroterpenoid pathways in the same species. << Less
J. Am. Chem. Soc. 138:12671-12677(2016) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.