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- Name help_outline (5S)-3-[(2E,6R,8E,10E,12E)-2,6-dimethyltetradeca-2,8,10,12-tetraenoyl]-5-(hydroxymethyl)pyrrolidine-2,4-dione Identifier CHEBI:169938 Charge -1 Formula C21H28NO4 InChIKeyhelp_outline GZZQDCWZFRVQLN-BIVXZIHOSA-N SMILEShelp_outline [C-]1(C(N[C@H](C1=O)CO)=O)C(/C(=C/CC[C@H](C/C=C/C=C/C=C/C)C)/C)=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 trichosetin Identifier CHEBI:142061 Charge -1 Formula C21H28NO4 InChIKeyhelp_outline TYCWBBBQIATAJE-GEZPOGBYSA-M SMILEShelp_outline C1C[C@H](C[C@@]2([C@@]1([C@@]([C@@](C=C2)(/C=C/C)[H])(\C(\[O-])=C/3\C(N[C@H](C3=O)CO)=O)C)[H])[H])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:67328 | RHEA:67329 | RHEA:67330 | RHEA:67331 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Chemo-enzymatic synthesis of equisetin.
Li X., Zheng Q., Yin J., Liu W., Gao S.
We here report that the biosynthesis of equisetin, a fungal tetramate natural product with potent anti-infectious activity, relies on Fsa2, a Diels-Alderase that constructs the trans-decalin system of the molecule in a stereo-selective manner. This finding led to the development of a concise chemo ... >> More
We here report that the biosynthesis of equisetin, a fungal tetramate natural product with potent anti-infectious activity, relies on Fsa2, a Diels-Alderase that constructs the trans-decalin system of the molecule in a stereo-selective manner. This finding led to the development of a concise chemo-enzymatic route toward the synthesis of equisetin, which involves facile preparation of a linear polyene precursor via 7-steps and Fsa2 activity for equisetin maturation through an intramolecular Diels-Alder reaction, thus exemplifying the significance of the combination of chemical and biological methods to achieve structurally complex cyclic natural products and their derivatives. << Less
Chem. Commun. (Camb.) 53:4695-4697(2017) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
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A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis.
Kato N., Nogawa T., Hirota H., Jang J.H., Takahashi S., Ahn J.S., Osada H.
Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjuga ... >> More
Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugated with an amino acid. PKS-NRPS hybrid complex programs to create structural diversity in the polyketide backbone have begun to be investigated, yet mechanism of control of the stereochemistry in a decalin formation via a Diels-Alder cycloaddition remains uncertain. Here, we demonstrate that fsa2, which showed no homology to genes encoding proteins of known function, in the fsa cluster responsible for equisetin and fusarisetin A biosynthesis in Fusarium sp. FN080326, is involved in the control of stereochemistry in decalin formation via a Diels-Alder reaction in the equisetin biosynthetic pathway. << Less
Biochem. Biophys. Res. Commun. 460:210-215(2015) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.