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- Name help_outline S-(2-succino)-L-cysteine Identifier CHEBI:143133 Charge -2 Formula C7H9NO6S InChIKeyhelp_outline XPKKFTKCRVIDAG-WUCPZUCCSA-L SMILEShelp_outline C([O-])([C@@H]([NH3+])CSC(C([O-])=O)CC([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 acetyl-CoA Identifier CHEBI:57288 (Beilstein: 8468140) help_outline Charge -4 Formula C23H34N7O17P3S InChIKeyhelp_outline ZSLZBFCDCINBPY-ZSJPKINUSA-J SMILEShelp_outline CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 361 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-acetyl-S-(2-succino)-L-cysteine Identifier CHEBI:144658 Charge -3 Formula C9H10NO7S InChIKeyhelp_outline VWRYIVZHCHQFKJ-ZBHICJROSA-K SMILEShelp_outline C([O-])([C@@H](NC(C)=O)CSC(C([O-])=O)CC(=O)[O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,511 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 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:61440 | RHEA:61441 | RHEA:61442 | RHEA:61443 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Identification of a metabolic disposal route for the oncometabolite S-(2-succino)cysteine in Bacillus subtilis.
Niehaus T.D., Folz J., McCarty D.R., Cooper A.J.L., Moraga Amador D., Fiehn O., Hanson A.D.
Cellular thiols such as cysteine spontaneously and readily react with the respiratory intermediate fumarate, resulting in the formation of stable <i>S</i>-(2-succino)-adducts. Fumarate-mediated succination of thiols increases in certain tumors and in response to glucotoxicity associated with diabe ... >> More
Cellular thiols such as cysteine spontaneously and readily react with the respiratory intermediate fumarate, resulting in the formation of stable <i>S</i>-(2-succino)-adducts. Fumarate-mediated succination of thiols increases in certain tumors and in response to glucotoxicity associated with diabetes. Therefore, <i>S</i>-(2-succino)-adducts such as <i>S</i>-(2-succino)cysteine (2SC) are considered oncometabolites and biomarkers for human disease. No disposal routes for <i>S</i>-(2-succino)-compounds have been reported prior to this study. Here, we show that <i>Bacillus subtilis</i> metabolizes 2SC to cysteine using a pathway encoded by the <i>yxe</i> operon. The first step is <i>N</i>-acetylation of 2SC followed by an oxygenation that we propose results in the release of oxaloacetate and <i>N</i>-acetylcysteine, which is deacetylated to give cysteine. Knockouts of the genes predicted to mediate each step in the pathway lose the ability to grow on 2SC as the sulfur source and accumulate the expected upstream metabolite(s). We further show that <i>N</i>-acetylation of 2SC relieves toxicity. This is the first demonstration of a metabolic disposal route for any <i>S</i>-(2-succino)-compound, paving the way toward the identification of corresponding pathways in other species. << Less
J. Biol. Chem. 293:8255-8263(2018) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.