Reaction participants Show >> << Hide
- Name help_outline (2S)-3-[(2S)-3,5-dioxo-4-[(2E,4R,6R,8E,10E,12E)-4,6,12-trimethyltetradeca-2,8,10,12-tetraenoyl]pyrrolidin-2-yl]-2-hydroxy-2-methylpropanoate Identifier CHEBI:167907 Charge -2 Formula C25H33NO6 InChIKeyhelp_outline XWIZBMORQRLANJ-MJZDXNEPSA-M SMILEShelp_outline C([C@@H](C/C=C/C=C/C(/C)=C/C)C)[C@H](/C=C/C([C-]1C([C@@H](NC1=O)C[C@](C(=O)[O-])(C)O)=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
- Name help_outline sch 210972 Identifier CHEBI:167897 Charge -2 Formula C25H33NO6 InChIKeyhelp_outline AVZATKWNGXCSDN-IIRHHVPJSA-L SMILEShelp_outline [H][C@]12C[C@@H](C)C[C@@H](C)[C@]1([H])[C@@H](\C([O-])=C1\C(=O)N[C@@H](C[C@](C)(O)C([O-])=O)C1=O)[C@]([H])(C=C2)C(\C)=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:67268 | RHEA:67269 | RHEA:67270 | RHEA:67271 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
Publications
-
Involvement of lipocalin-like CghA in decalin-forming stereoselective intramolecular [4+2] cycloaddition.
Sato M., Yagishita F., Mino T., Uchiyama N., Patel A., Chooi Y.H., Goda Y., Xu W., Noguchi H., Yamamoto T., Hotta K., Houk K.N., Tang Y., Watanabe K.
Understanding enzymatic Diels-Alder (DA) reactions that can form complex natural product scaffolds is of considerable interest. Sch 210972 1, a potential anti-HIV fungal natural product, contains a decalin core that is proposed to form through a DA reaction. We identified the gene cluster responsi ... >> More
Understanding enzymatic Diels-Alder (DA) reactions that can form complex natural product scaffolds is of considerable interest. Sch 210972 1, a potential anti-HIV fungal natural product, contains a decalin core that is proposed to form through a DA reaction. We identified the gene cluster responsible for the biosynthesis of 1 and heterologously reconstituted the biosynthetic pathway in Aspergillus nidulans to characterize the enzymes involved. Most notably, deletion of cghA resulted in a loss of stereoselective decalin core formation, yielding both an endo (1) and a diastereomeric exo adduct of the proposed DA reaction. Complementation with cghA restored the sole formation of 1. Density functional theory computation of the proposed DA reaction provided a plausible explanation of the observed pattern of product formation. Based on our study, we propose that lipocalin-like CghA is responsible for the stereoselective intramolecular [4+2] cycloaddition that forms the decalin core of 1. << Less
ChemBioChem 16:2294-2298(2015) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
-
Biosynthesis of the tetramic acids Sch210971 and Sch210972.
Kakule T.B., Zhang S., Zhan J., Schmidt E.W.
A biosynthetic pathway to fungal polyketide-nonribosomal peptide natural products, Sch210971 (1a) and Sch210972 (1b) from Hapsidospora irregularis, was characterized by reconstitution and heterologous expression in Fusarium heterosporum. Using genetic, biochemical, and feeding experiments, we show ... >> More
A biosynthetic pathway to fungal polyketide-nonribosomal peptide natural products, Sch210971 (1a) and Sch210972 (1b) from Hapsidospora irregularis, was characterized by reconstitution and heterologous expression in Fusarium heterosporum. Using genetic, biochemical, and feeding experiments, we show that the incorporated amino acid 4-hydroxyl-4-methyl glutamate (HMG) is synthesized by an aldolase, probably using pyruvate as the precursor. << Less
Org. Lett. 17:2295-2297(2015) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.