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- Name help_outline 2,3,4,7,9-pentahydroxy-6-methyl-1H-phenalen-1-one Identifier CHEBI:142788 Charge -1 Formula C14H9O6 InChIKeyhelp_outline WKCIPEFSZITGMF-UHFFFAOYSA-M SMILEShelp_outline C=12C(=CC(=C3C1C(C(C(=C2[O-])O)=O)=C(C=C3O)O)C)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
- Name help_outline dimethylallyl diphosphate Identifier CHEBI:57623 (Beilstein: 5288443; CAS: 22679-02-3) help_outline Charge -3 Formula C5H9O7P2 InChIKeyhelp_outline CBIDRCWHNCKSTO-UHFFFAOYSA-K SMILEShelp_outline CC(C)=CCOP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 77 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2,4,7,9-tetrahydroxy-6-methyl-8-(2-methylbut-3-en-2-yl)-1-oxo-1H-phenalen-3-ol Identifier CHEBI:145870 Charge -1 Formula C19H17O6 InChIKeyhelp_outline CVTRCJLWCGBOMT-UHFFFAOYSA-M SMILEShelp_outline C1=2C=3C(=C(C(=C1O)C(C=C)(C)C)O)C(C(=C(C3C(=CC2C)O)[O-])O)=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
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,085 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62656 | RHEA:62657 | RHEA:62658 | RHEA:62659 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Enzyme-catalyzed intramolecular enantioselective hydroalkoxylation.
Gao S.S., Garcia-Borras M., Barber J.S., Hai Y., Duan A., Garg N.K., Houk K.N., Tang Y.
Hydroalkoxylation is a powerful and efficient method of forming C-O bonds and cyclic ethers in synthetic chemistry. In studying the biosynthesis of the fungal natural product herqueinone, we identified an enzyme that can perform an intramolecular enantioselective hydroalkoxylation reaction. PhnH c ... >> More
Hydroalkoxylation is a powerful and efficient method of forming C-O bonds and cyclic ethers in synthetic chemistry. In studying the biosynthesis of the fungal natural product herqueinone, we identified an enzyme that can perform an intramolecular enantioselective hydroalkoxylation reaction. PhnH catalyzes the addition of a phenol to the terminal olefin of a reverse prenyl group to give a dihydrobenzofuran product. The enzyme accelerates the reaction by 3 × 10<sup>5</sup>-fold compared to the uncatalyzed reaction. PhnH belongs to a superfamily of proteins with a domain of unknown function (DUF3237), of which no member has a previously verified function. The discovery of PhnH demonstrates that enzymes can be used to promote the enantioselective hydroalkoxylation reaction and form cyclic ethers. << Less
J. Am. Chem. Soc. 139:3639-3642(2017) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.