Reaction participants Show >> << Hide
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Namehelp_outline
N-[(4E,6E,10S,12Z,14E)-6,10-dimethyl-3-oxohexadeca-4,6,12,14-tetraenoyl]-L-tyrosyl-[ACP]
Identifier
RHEA-COMP:16623
Reactive part
help_outline
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Name help_outline
O-(S-{N-[(4E,6E,10S,12Z,14E)-6,10-dimethyl-3-oxohexadeca-4,6,12,14-tetraenoyl]-L-tyrosyl}pantetheine-4
-phosphoryl)serine residue Identifier CHEBI:155893 Charge -1 Formula C41H58N4O12PS SMILEShelp_outline O=C([C@@H](NC(CC(/C=C/C(=C/CC[C@@H](C/C=C\C=C\C)C)/C)=O)=O)CC1=CC=C(C=C1)O)SCCNC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)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
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Name help_outline
O-(S-{N-[(4E,6E,10S,12Z,14E)-6,10-dimethyl-3-oxohexadeca-4,6,12,14-tetraenoyl]-L-tyrosyl}pantetheine-4
- Name help_outline (3E,5S)-3-[(2E,4E,8S,10E,12Z)-1-hydroxy-4,8-dimethyltetradeca-2,4,10,12-tetraen-1-ylidene]-5-[(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione Identifier CHEBI:155890 Charge -1 Formula C27H32NO4 InChIKeyhelp_outline YSSAANFDQOSWCH-KTTQBTPYSA-M SMILEShelp_outline C(=C/C(=C/CC[C@H](C)C/C=C/C=C\C)/C)\C(=C/1\C([C@@H](NC1=O)CC=2C=CC(=CC2)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
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Namehelp_outline
holo-[ACP]
Identifier
RHEA-COMP:9685
Reactive part
help_outline
- Name help_outline O-(pantetheine-4ʼ-phosphoryl)-L-serine residue Identifier CHEBI:64479 Charge -1 Formula C14H25N3O8PS SMILEShelp_outline C(NC(CCNC(=O)[C@@H](C(COP(OC[C@@H](C(*)=O)N*)(=O)[O-])(C)C)O)=O)CS 2D coordinates Mol file for the small molecule Search links Involved in 207 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:64548 | RHEA:64549 | RHEA:64550 | RHEA:64551 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Heterologous expression of ilicicolin H biosynthetic gene cluster and production of a new potent antifungal reagent, ilicicolin J.
Lin X., Yuan S., Chen S., Chen B., Xu H., Liu L., Li H., Gao Z.
Ilicicolin H is a broad-spectrum antifungal agent targeting mitochondrial cytochrome bc1 reductase. Unfortunately, ilicicolin H shows reduced activities in vivo. Here, we report our effort on the identification of ilicicolin H biosynthetic gene cluster (BGC) by genomic sequencing a producing strai ... >> More
Ilicicolin H is a broad-spectrum antifungal agent targeting mitochondrial cytochrome bc1 reductase. Unfortunately, ilicicolin H shows reduced activities in vivo. Here, we report our effort on the identification of ilicicolin H biosynthetic gene cluster (BGC) by genomic sequencing a producing strain, <i>Neonectria</i> sp. DH2, and its heterologous production in <i>Aspergillus nidulans</i>. In addition, a shunt product with similar antifungal activities, ilicicolin J, was uncovered. This effort would provide a base for future combinatorial biosynthesis of ilicicolin H analogues. Bioinformatics analysis suggests that the backbone of ilicicolin H is assembled by a polyketide-nonribosomal peptide synthethase (IliA), and then offloaded with a tetramic acid moiety. Similar to tenellin biosynthesis, the tetramic acid is then converted to pyridone by a putative P450, IliC. The decalin portion is most possibly constructed by a <i>S</i>-adenosyl-l-methionine (SAM)-dependent Diels-Alderase (IliD). << Less
Molecules 24:0-0(2019) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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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.