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- 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 (2'R)-atrovenetin Identifier CHEBI:145872 Charge -1 Formula C19H17O6 InChIKeyhelp_outline QQCGLXMFCOVAAG-SSDOTTSWSA-M SMILEShelp_outline C12=C3C(=C(C4=C1O[C@@H](C4(C)C)C)O)C(C(=C(C3=C(C=C2C)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
Cross-references
| RHEA:62660 | RHEA:62661 | RHEA:62662 | RHEA:62663 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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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.
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Crystal structure and proposed mechanism of an enantioselective hydroalkoxylation enzyme from Penicillium herquei.
Feng Y., Yu X., Huang J.W., Liu W., Li Q., Hu Y., Yang Y., Chen Y., Jin J., Li H., Chen C.C., Guo R.T.
Hydroalkoxylation is a useful and efficient reaction which generates C-O bond and produces cyclic ethers, the common structural elements of natural products. The dedicative enzyme which can catalyze enantioselective hydroalkoxylation named PhnH was recently identified in the herqueinone biosynthet ... >> More
Hydroalkoxylation is a useful and efficient reaction which generates C-O bond and produces cyclic ethers, the common structural elements of natural products. The dedicative enzyme which can catalyze enantioselective hydroalkoxylation named PhnH was recently identified in the herqueinone biosynthetic gene from Penicillium herquei. It catalyzes addition of a phenol to the terminal olefin on substrate to produce a dihydrobenzofuran. Here, the crystal structure of PhnH is reported and the putative substrate-binding pocket is illustrated. Through docking experiment, possible substrate-binding poses are displayed and the catalytic mechanism is therefore proposed. Our findings form the basis for further studies of enantioselective hydroalkoxylation enzymes. << Less
Biochem Biophys Res Commun 516:801-805(2019) [PubMed] [EuropePMC]