Enzymes
| UniProtKB help_outline | 1 proteins |
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- Name help_outline 8-epi-ilicicolin H Identifier CHEBI:155888 Charge 0 Formula C27H31NO4 InChIKeyhelp_outline BYVVOONSAAQMKI-NMEWZTTESA-N SMILEShelp_outline [C@H]1([C@@H]([C@@]2([C@@](C(=C1)C)(CC[C@@H](C2)C)[H])[H])/C=C/C)C(C3=C(C(C=4C=CC(=CC4)O)=CNC3=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 ilicicolin H Identifier CHEBI:77772 Charge 0 Formula C27H31NO4 InChIKeyhelp_outline BYVVOONSAAQMKI-RFKCMYLBSA-N SMILEShelp_outline C\C=C\[C@@H]1[C@H]2C[C@@H](C)CC[C@@H]2C(C)=C[C@H]1C(=O)c1c(O)c(c[nH]c1=O)-c1ccc(O)cc1 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:64564 | RHEA:64565 | RHEA:64566 | RHEA:64567 | |
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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 inverse-electron demand Diels-Alder reaction in the biosynthesis of antifungal ilicicolin H.
Zhang Z., Jamieson C.S., Zhao Y.L., Li D., Ohashi M., Houk K.N., Tang Y.
The pericyclases are a growing superfamily of enzymes that catalyze pericyclic reactions. We report a pericyclase IccD catalyzing an inverse-electron demand Diels-Alder (IEDDA) reaction with a rate acceleration of 3 × 10<sup>5</sup>-fold in the biosynthesis of fungal natural product ilicicolin H. ... >> More
The pericyclases are a growing superfamily of enzymes that catalyze pericyclic reactions. We report a pericyclase IccD catalyzing an inverse-electron demand Diels-Alder (IEDDA) reaction with a rate acceleration of 3 × 10<sup>5</sup>-fold in the biosynthesis of fungal natural product ilicicolin H. We demonstrate IccD is highly periselective toward the IEDDA cycloaddition over a competing normal electron demand Diels-Alder (NEDDA) reaction from an ambimodal transition state. A predicted flavoenzyme IccE was identified to epimerize the IEDDA product 8-epi-ilicicolin H to ilicicolin H, a step that is critical for the observed antifungal activity of ilicicolin H. Our results reveal the ilicicolin H biosynthetic pathway and add to the collection of pericyclic reactions that are catalyzed by pericyclases. << Less
J. Am. Chem. Soc. 141:5659-5663(2019) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.