| Revision as of 13:38, 12 June 2011 editZéroBot (talk | contribs)704,777 editsm r2.7.1) (robot Adding: fr:Acide cystéine-sulfinique← Previous edit |
Latest revision as of 09:26, 15 April 2024 edit undo149.171.156.235 (talk) Changed "only the D-enantiomer eixsts in nature" to "L-enantiomer". Only L-amino acids are found in living organisms.Tag: Visual edit |
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| verifiedrevid = 426623481 |
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| verifiedrevid = 433880904 |
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| ImageFile = 3-Sulfino-L-alanine.svg |
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| ImageFile = 3-Sulfino-L-alanine.svg |
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| ImageSize = |
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| ImageSize = |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = L-Cysteine-sulfinic-acid-3D-balls.png |
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| ImageFile1 = L-Cysteine-sulfinic-acid-3D-balls.png |
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| ImageSize1 = 150px |
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| ImageSize1 = 150px |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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|IUPACName=2-amino-3-sulfinopropanoic acid |
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| IUPACName=2-amino-3-sulfinopropanoic acid |
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|OtherNames= |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{Cascite|changed|CAS}} |
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| CASNo=2381-08-0 |
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| CASNo = 1115-65-7 |
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| PubChem=109 |
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| CASNo1=2381-08-0 |
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| SMILES=C(C(C(=O)O)N)S(=O)O |
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| index1_label=unspecified stereocentres |
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| MeSHName=cysteine+sulfinic+acid |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 1266065 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16345 |
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| ChEMBL = 1160508 |
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| DrugBank = DB02153 |
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| IUPHAR_ligand = 5447 |
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| KEGG = C00606 |
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| MeSHName=cysteine+sulfinic+acid |
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| PubChem = 1549098 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = UZY4HYK4ZX |
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| SMILES = O=C(O)(N)CS(=O)O |
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| InChI = 1/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 |
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| InChIKey = ADVPTQAUNPRNPO-REOHCLBHBM |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ADVPTQAUNPRNPO-REOHCLBHSA-N |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>3</sub>H<sub>7</sub>NO<sub>4</sub>S |
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| Formula=C<sub>3</sub>H<sub>7</sub>NO<sub>4</sub>S |
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| MolarMass=153.15698 |
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| MolarMass=153.15698 |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Cysteine sulfinic acid''' is the ] with the nominal formula HO<sub>2</sub>SCH<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H . It is a rare example of an ] bearing a sulfinic acid ]. It is a white solid that is soluble in water. Like most natural amino acids, it is chiral, only the L-enantiomer occurs in nature, and it exists as the zwitterion at neutral pH. It is an intermediate in ]. It is not a coded amino acid, but is produced ]ly. Peptides containing the cysteine sulfinic acid residue are substrates for ].<ref>{{cite journal |doi=10.1038/s41589-018-0116-2|title=Chemical proteomics reveals new targets of cysteine sulfinic acid reductase|year=2018|last1=Akter|first1=Salma|last2=Fu|first2=Ling|last3=Jung|first3=Youngeun|last4=Conte|first4=Mauro Lo|last5=Lawson|first5=J. Reed|last6=Lowther|first6=W. Todd|last7=Sun|first7=Rui|last8=Liu|first8=Keke|last9=Yang|first9=Jing|last10=Carroll|first10=Kate S.|journal=Nature Chemical Biology|volume=14|issue=11|pages=995–1004|pmid=30177848|pmc=6192846}}</ref> |
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'''Cysteine sulfinic acid''' is an intermediate in ]. |
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Cysteine sulfinic acid is derived from ]. Cysteine is formed from ] via the ] enzyme, and is either broken down by ] or cystathionine gamma-lyase or enters the cysteine sulfinic acid pathway where it is oxidized by ] to form cysteine sulfinic acid. Cysteine sulfinic acid, in turn, is decarboxylated by ] to form ], which in turn is oxidized by ] to yield taurine.<ref>{{Cite journal | author = Sumizu K | date = 1962 | title = Oxidation of hypotaurine in rat liver | journal = Biochim. Biophys. Acta | volume = 63 | pages = 210–212 | doi = 10.1016/0006-3002(62)90357-8 | pmid=13979247}}</ref> Proteins containing this residue are found at the active site of some ]s.<ref>Isao Endo, Masaki Nojiri, b, Masanari Tsujimura, Masayoshi Nakasako, Shigehiro Nagashima, Masafumi Yohda, Masafumi Odaka "Focused Review: Fe-type nitrile hydratase"Journal of Inorganic Biochemistry 2001, Volume 83, Issue 4, February 2001, Pages 247–253. {{doi|10.1016/S0162-0134(00)00171-9}}</ref> |
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It is formed by ]. |
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]{{clear-left}} |
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==References== |
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<references/> |
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{{Amino acid metabolism intermediates}} |
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{{Amino acid metabolism intermediates}} |
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] |
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{{organic-compound-stub}} |
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