Enzymes
| UniProtKB help_outline | 1 proteins |
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- Name help_outline (1'E,3'E)-5-(3,3-dimethyloxiran-2-yl)-3-methylhexa-1,3-dienyl-quinolinone B Identifier CHEBI:193561 Charge 0 Formula C27H31NO6 InChIKeyhelp_outline BJXAHPRMTWSZRG-MKGCGASNSA-N SMILEShelp_outline O[C@]1([C@@H](OC)C(=O)NC2=C1C(O)=C(C=C2)/C=C/C(=C/CC3C(C)(C)O3)/C)C4=CC=C(OC)C=C4 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline aspoquinolone B Identifier CHEBI:193562 Charge 0 Formula C27H31NO6 InChIKeyhelp_outline AISVMTZASACEBH-YCFXYUOFSA-N SMILEShelp_outline O1C([C@@]2([C@@](C2)([C@@]1(C)/C=C/C3=C(O)C=4[C@@](O)([C@@H](OC)C(=O)NC4C=C3)C5=CC=C(OC)C=C5)[H])[H])(C)C 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:74515 | RHEA:74516 | RHEA:74517 | RHEA:74518 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Enzyme-catalyzed cationic epoxide rearrangements in quinolone alkaloid biosynthesis.
Zou Y., Garcia-Borras M., Tang M.C., Hirayama Y., Li D.H., Li L., Watanabe K., Houk K.N., Tang Y.
Epoxides are highly useful synthons and biosynthons for the construction of complex natural products during total synthesis and biosynthesis, respectively. Among enzyme-catalyzed epoxide transformations, a reaction that is notably missing, in regard to the synthetic toolbox, is cationic rearrangem ... >> More
Epoxides are highly useful synthons and biosynthons for the construction of complex natural products during total synthesis and biosynthesis, respectively. Among enzyme-catalyzed epoxide transformations, a reaction that is notably missing, in regard to the synthetic toolbox, is cationic rearrangement that takes place under strong acid. This is a challenging transformation for enzyme catalysis, as stabilization of the carbocation intermediate upon epoxide cleavage is required. Here, we discovered two Brønsted acid enzymes that can catalyze two unprecedented epoxide transformations in biology. PenF from the penigequinolone pathway catalyzes a cationic epoxide rearrangement under physiological conditions to generate a quaternary carbon center, while AsqO from the aspoquinolone pathway catalyzes a 3-exo-tet cyclization to forge a cyclopropane-tetrahydrofuran ring system. The discovery of these new epoxide-modifying enzymes further highlights the versatility of epoxides in complexity generation during natural product biosynthesis. << Less
Nat. Chem. Biol. 13:325-332(2017) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.