Reaction participants Show >> << Hide
- Name help_outline stemphyloxin I Identifier CHEBI:145070 (CAS: 81210-11-9) help_outline Charge 0 Formula C21H34O6 InChIKeyhelp_outline YRECHDUAXCBBOZ-HOCCXODSSA-N SMILEShelp_outline [C@]1([C@H]([C@](C([C@@]2([C@@]1([C@@H](C[C@](C2)(O)C)C)[H])[H])=O)(C)O)[C@@H](CC)CO)(C(=O)/C=C\O)C 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 stemphyloxin II Identifier CHEBI:145066 Charge 0 Formula C21H34O6 InChIKeyhelp_outline JTFGPTHCAAUOQL-RNPLJHCFSA-N SMILEShelp_outline [C@]12(C(/C(/[C@]([C@@]3([C@@]1([C@@](C[C@](C3)(O)C)(C)[H])[H])[H])(O)[C@@]([C@@]2([C@@H](CC)CO)[H])(C)O)=C\O)=O)C 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:62716 | RHEA:62717 | RHEA:62718 | RHEA:62719 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Biosynthesis of a Tricyclo[6.2.2.02,7]dodecane System by a Berberine Bridge Enzyme-like Intramolecular Aldolase.
Li H., Hu J., Wei H., Solomon P.S., Stubbs K.A., Chooi Y.H.
The aldol reaction is one of the most fundamental stereocontrolled carbon-carbon bond-forming reactions and is mainly catalyzed by aldolases in nature. Despite the fact that the aldol reaction has been widely proposed to be involved in fungal secondary metabolite biosynthesis, a dedicated aldolase ... >> More
The aldol reaction is one of the most fundamental stereocontrolled carbon-carbon bond-forming reactions and is mainly catalyzed by aldolases in nature. Despite the fact that the aldol reaction has been widely proposed to be involved in fungal secondary metabolite biosynthesis, a dedicated aldolase that catalyzes stereoselective aldol reactions has only rarely been reported in fungi. Herein, we activated a cryptic polyketide biosynthetic gene cluster that was upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection; this resulted in the production of the phytotoxic stemphyloxin II (1). Through heterologous reconstruction of the biosynthetic pathway and in vitro assay by using cell-free lysate from Aspergillus nidulans, we demonstrated that a berberine bridge enzyme (BBE)-like protein SthB catalyzes an intramolecular aldol reaction to establish the bridged tricyclo[6.2.2.0<sup>2,7</sup> ]dodecane skeleton in the post-assembly tailoring step. The characterization of SthB as an aldolase enriches the catalytic toolbox of classic reactions and the functional diversities of the BBE superfamily of enzymes. << Less
Chemistry 25:15062-15066(2019) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.