Cysteine sulfinic acid

Names
IUPAC name

2-amino-3-sulfinopropanoic acid

Identifiers

CAS Number

* 1115-65-7 N
* unspecified stereocentres: 2381-08-0

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:16345 Y

ChEMBL |

* ChEMBL1160508

ChemSpider |

* 1266065 N

DrugBank |

* DB02153

IUPHAR/BPS

* 5447

KEGG |

* C00606

MeSH | cysteine+sulfinic+acid

PubChem CID

* 1549098

UNII |

* UZY4HYK4ZX Y

InChI

* InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1 N

Key: ADVPTQAUNPRNPO-REOHCLBHSA-N N

* InChI=1/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1

Key: ADVPTQAUNPRNPO-REOHCLBHBM

SMILES

* O=C(O)[C@@H](N)CS(=O)O

Properties

Chemical formula

| C3H7NO4S
Molar mass | 153.15698

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Cysteine sulfinic acid is the organic compound with the nominal formula HO2SCH2CH(NH2)CO2H . It is a rare example of an amino acid bearing a sulfinic acid functional group. 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 cysteine metabolism. It is not a coded amino acid, but is produced post-translationally.[1]

Cysteine is oxidized by cysteine dioxygenase to form cysteine sulfinic acid. Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine, which in turn is oxidized by hypotaurine dehydrogenase to yield taurine.[2] Proteins containing this residue are found at the active site of some nitrile hydratases.[3]

Cysteine sulfinic acid (2) is an intermediate in the conversion of cysteine (1) to taurine (4).

Peptides containing the cysteine sulfinic acid residue are substrates for cysteine sulfinic acid reductase.[4]

## References

1. ↑ Hayward, Laura; Baud, Matthias G. J. (2025). "Cysteine sulfinic acid and sulfinylated peptides". RSC Chemical Biology 6 (7): 1019–1033. doi:10.1039/D5CB00040H. PMID 40406162.
2. ↑ Sumizu K (1962). "Oxidation of hypotaurine in rat liver". Biochim. Biophys. Acta 63: 210–212. doi:10.1016/0006-3002(62)90357-8. PMID 13979247.
3. ↑ 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
4. ↑ Akter, Salma; Fu, Ling; Jung, Youngeun; Conte, Mauro Lo; Lawson, J. Reed; Lowther, W. Todd; Sun, Rui; Liu, Keke et al. (2018). "Chemical proteomics reveals new targets of cysteine sulfinic acid reductase". Nature Chemical Biology 14 (11): 995–1004. doi:10.1038/s41589-018-0116-2. PMID 30177848.

* v
* t
* e

Amino acid metabolism metabolic intermediates

K→acetyl-CoA|

| lysine→|

* Saccharopine
* Allysine
* α-Aminoadipic acid
* α-Ketoadipate
* Glutaryl-CoA
* Glutaconyl-CoA
* Crotonyl-CoA
* β-Hydroxybutyryl-CoA

|

leucine→|

* β-Hydroxy β-methylbutyric acid
* β-Hydroxy β-methylbutyryl-CoA
* Isovaleryl-CoA
* α-Ketoisocaproic acid
* β-Ketoisocaproic acid
* β-Ketoisocaproyl-CoA
* β-Leucine
* β-Methylcrotonyl-CoA
* β-Methylglutaconyl-CoA
* β-Hydroxy β-methylglutaryl-CoA

tryptophan→alanine→|

* N'-Formylkynurenine
* Kynurenine
* Anthranilic acid
* 3-Hydroxykynurenine
* 3-Hydroxyanthranilic acid
* 2-Amino-3-carboxymuconic semialdehyde
* 2-Aminomuconic semialdehyde
* 2-Aminomuconic acid
* Glutaryl-CoA

| G→pyruvate→citrate|

| glycine→serine→|

* 3-Phosphoglyceric acid

* glycine→creatine: Glycocyamine
* Phosphocreatine
* Creatinine

|

G→glutamate→
α-ketoglutarate|

| histidine→|

* Urocanic acid
* Imidazol-4-one-5-propionic acid
* Formiminoglutamic acid
* Glutamate-1-semialdehyde

|

proline→|

* 1-Pyrroline-5-carboxylic acid

arginine→|

* Agmatine
* Ornithine
* Citrulline
* Cadaverine
* Putrescine

other|

* cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA|

| valine→|

* α-Ketoisovaleric acid
* Isobutyryl-CoA
* Methacrylyl-CoA
* 3-Hydroxyisobutyryl-CoA
* 3-Hydroxyisobutyric acid
* 2-Methyl-3-oxopropanoic acid

|

isoleucine→|

* 2,3-Dihydroxy-3-methylpentanoic acid
* 2-Methylbutyryl-CoA
* Tiglyl-CoA
* 2-Methylacetoacetyl-CoA

methionine→|

* generation of homocysteine: S-Adenosyl methionine
* S-Adenosyl-L-homocysteine
* Homocysteine

* conversion to cysteine: Cystathionine
* α-Ketobutyric acid+Cysteine

threonine→|

* α-Ketobutyric acid

propionyl-CoA→|

* Methylmalonyl-CoA

G→fumarate|

| [[Chemistry:Phenylphenylalanine]]→tyrosine→|

* 4-Hydroxyphenylpyruvic acid
* Homogentisic acid
* 4-Maleylacetoacetic acid

|

G→oxaloacetate|

* see urea cycle

Other|

| Cysteine metabolism|

* Cysteine sulfinic acid

|

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