Reaction participants Show >> << Hide
- Name help_outline o-quinone methide Identifier CHEBI:188927 Charge 0 Formula C10H10O3 InChIKeyhelp_outline KPYMODXRSSIYIB-UHFFFAOYSA-N SMILEShelp_outline C=1(C(C(C(=CC1C(=O)C)C)=O)=C)O 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ethanol Identifier CHEBI:16236 (CAS: 64-17-5) help_outline Charge 0 Formula C2H6O InChIKeyhelp_outline LFQSCWFLJHTTHZ-UHFFFAOYSA-N SMILEShelp_outline CCO 2D coordinates Mol file for the small molecule Search links Involved in 23 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline hydroxyclavatol ethyl ether Identifier CHEBI:188929 Charge 0 Formula C12H16O4 InChIKeyhelp_outline NQEKHQQEPLPUST-UHFFFAOYSA-N SMILEShelp_outline C=1(C(=C(C(=CC1C(=O)C)C)O)COCC)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:70091 | RHEA:70092 | RHEA:70093 | RHEA:70094 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Peniphenone and penilactone formation in Penicillium crustosum via 1,4-Michael additions of ortho-quinone methide from hydroxyclavatol to gamma-butyrolactones from Crustosic Acid.
Fan J., Liao G., Kindinger F., Ludwig-Radtke L., Yin W.B., Li S.M.
Penilactones A and B consist of a γ-butyrolactone and two clavatol moieties. We identified two separate gene clusters for the biosynthesis of these key building blocks in Penicillium crustosum. Gene deletion, feeding experiments, and biochemical investigations proved that a nonreducing PKS ClaF is ... >> More
Penilactones A and B consist of a γ-butyrolactone and two clavatol moieties. We identified two separate gene clusters for the biosynthesis of these key building blocks in Penicillium crustosum. Gene deletion, feeding experiments, and biochemical investigations proved that a nonreducing PKS ClaF is responsible for the formation of clavatol and the PKS-NRPS hybrid TraA is involved in the formation of crustosic acid, which undergoes decarboxylation and isomerization to the predominant terrestric acid. Both acids are proposed to be converted to γ-butyrolactones with involvement of a cytochrome P<sub>450</sub> ClaJ. Oxidation of clavatol to hydroxyclavatol by a nonheme Fe<sup>II</sup>/2-oxoglutarate-dependent oxygenase ClaD and its spontaneous dehydration to an ortho-quinone methide initiate the two nonenzymatic 1,4-Michael addition steps. Spontaneous addition of the methide to the γ-butyrolactones led to peniphenone D and penilactone D, which undergo again stereospecific attacking by methide to give penilactones A/B. << Less
J. Am. Chem. Soc. 141:4225-4229(2019) [PubMed] [EuropePMC]
This publication is cited by 8 other entries.
Comments
This reaction can occur spontaneously.