Reaction participants Show >> << Hide
- Name help_outline 2-hydroxyethane-1-sulfonate Identifier CHEBI:61904 Charge -1 Formula C2H5O4S InChIKeyhelp_outline SUMDYPCJJOFFON-UHFFFAOYSA-M SMILEShelp_outline OCCS([O-])(=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,285 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 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,279 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline sulfoacetaldehyde Identifier CHEBI:58246 Charge -1 Formula C2H3O4S InChIKeyhelp_outline JTJIXCMSHWPJJE-UHFFFAOYSA-M SMILEShelp_outline [H]C(=O)CS([O-])(=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 11 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:29591 | RHEA:29592 | RHEA:29593 | RHEA:29594 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Isethionate as a product from taurine during nitrogen-limited growth of Klebsiella oxytoca TauN1.
Styp von Rekowski K., Denger K., Cook A.M.
Klebsiella oxytoca TauN1 represents a group of isolates which utilise taurine (2-aminoethanesulfonate) quantitatively as a sole source of combined nitrogen for aerobic growth. During growth, a compound is excreted, which has now been identified as isethionate (2-hydroxyethanesulfonate). An ion-chr ... >> More
Klebsiella oxytoca TauN1 represents a group of isolates which utilise taurine (2-aminoethanesulfonate) quantitatively as a sole source of combined nitrogen for aerobic growth. During growth, a compound is excreted, which has now been identified as isethionate (2-hydroxyethanesulfonate). An ion-chromatographic separation of isethionate was developed to quantify the putative isethionate, whose identity was confirmed by matrix-assisted, laser-desorption ionisation time-of-flight mass spectrometry. Strain TauN1 utilised taurine (and excreted isethionate) concomitantly with growth. Cell-free extracts contained inducible taurine transaminase, which yielded sulfoacetaldehyde. A soluble, NADP-dependent isethionate dehydrogenase converted sulfoacetaldehyde to isethionate. The enzyme was partially purified and it apparently belonged to the family of short-chain alcohol dehydrogenases. << Less
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Isethionate formation from taurine in Chromohalobacter salexigens: purification of sulfoacetaldehyde reductase.
Krejcik Z., Hollemeyer K., Smits T.H., Cook A.M.
Bacterial generation of isethionate (2-hydroxyethanesulfonate) from taurine (2-aminoethanesulfonate) by anaerobic gut bacteria was established in 1980. That phenomenon in pure culture was recognized as a pathway of assimilation of taurine-nitrogen. Based on the latter work, we predicted from genom ... >> More
Bacterial generation of isethionate (2-hydroxyethanesulfonate) from taurine (2-aminoethanesulfonate) by anaerobic gut bacteria was established in 1980. That phenomenon in pure culture was recognized as a pathway of assimilation of taurine-nitrogen. Based on the latter work, we predicted from genome-sequence data that the marine gammaproteobacterium Chromohalobacter salexigens DSM 3043 would exhibit this trait. Quantitative conversion of taurine to isethionate, identified by mass spectrometry, was confirmed, and the taurine-nitrogen was recovered as cell material. An eight-gene cluster was predicted to encode the inducible vectorial, scalar and regulatory enzymes involved, some of which were known from other taurine pathways. The genes (Csal_0153-Csal_0156) encoding a putative ATP-binding-cassette (ABC) transporter for taurine (TauAB(1)B(2)C) were shown to be inducibly transcribed by reverse transcription (RT-) PCR. An inducible taurine : 2-oxoglutarate aminotransferase [EC 2.6.1.55] was found (Csal_0158); the reaction yielded glutamate and sulfoacetaldehyde. The sulfoacetaldehyde was reduced to isethionate by NADPH-dependent sulfoacetaldehyde reductase (IsfD), a member of the short-chain alcohol dehydrogenase superfamily. The 27 kDa protein (SDS-PAGE) was identified by peptide-mass fingerprinting as the gene product of Csal_0161. The putative exporter of isethionate (IsfE) is encoded by Csal_0160; isfE was inducibly transcribed (RT-PCR). The presumed transcriptional regulator, TauR (Csal_0157), may autoregulate its own expression, typical of GntR-type regulators. Similar gene clusters were found in several marine and terrestrial gammaproteobacteria, which, in the gut canal, could be the source of not only mammalian, but also arachnid and cephalopod isethionate. << Less