PRODUCTS

3-SULFOALANINE

3-sulfoalanine is an amino acid produced by the oxidation of cysteine, where the thiol group is fully oxidized to a sulfonic acid group.
3-sulfoalanine is a biosynthetic precursor to taurine in microalgae, while most taurine in animals is derived from cysteine sulfinate.
3-sulfoalanine plays a role in taurine and hypotaurine metabolism and exists in all living species, ranging from bacteria to humans.

CAS Number: 498-40-8
EC Number: 207-861-3
Molecular Formula: C3H7NO5S
Molecular Weight (g/mol): 169.15

Synonyms: DL-CYSTEIC ACID, 2-amino-3-sulfopropanoic acid, 13100-82-8, cysteate, beta-Sulfoalanine, Alanine, 3-sulfo-, 3024-83-7, Cysteinic acid, Cepteic acid, Cipteic acid, Cysteric acid, A3OGP4C37W, CHEBI:21260, Cysteinesulfonate, 2-amino-3-sulfopropanoate, L-Cysteate, UNII-A3OGP4C37W, cysteinsaure, Cepteate, Cipteate, Cysterate, NSC 254030, NSC-254030, L-Cysteic acid, 8, 3-Sulfoalanine, (L)-, 2-Amino-3-sulfopropionate, CYSTEIC ACID [MI], CYSTEIC ACID, DL-, CHEMPACIFIC41266, SCHEMBL44030,m2-amino-3-sulfopro-panoic acid, CHEMBL1171434, 2-azanyl-3-sulfo-propanoic acid, BDBM85473, DTXSID40862048, XVOYSCVBGLVSOL-UHFFFAOYSA-N, BBL100099, MFCD00065088, NSC254030, STL301905, AKOS005174455, 3-Sulfoalanine (H-DL-Cys(O3H)-OH), LS-04435, FT-0627746, FT-0655399, FT-0683826, C-9550, EN300-717791, A820275, Q2823250, Z1198149799, InChI=1/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9, 13100-82-8 [RN], 2-amino-3-sulfopropanoic acid, 3024-83-7 [RN], 3-Sulfoalanin [German] [ACD/IUPAC Name], 3-Sulfoalanine [ACD/IUPAC Name], 3-Sulfoalanine [French] [ACD/IUPAC Name], A3OGP4C37W, a-Amino-b-sulfopropionic Acid, Alanine, 3-sulfo- [ACD/Index Name], CYA, Cysteic Acid, Cysteic acid (VAN), CYSTEIC ACID, D-, CYSTEIC ACID, DL-, CYSTEIC ACID, L-, DL-cysteic acid, L-Cysteic Acid, UNII:A3OGP4C37W, α-amino-β-sulfopropionic acid, 2-Amino-3-sulfopropanoate [ACD/IUPAC Name], 2-Amino-3-sulfopropionate, Cepteate, Cipteate, Cysteinesulfonate, Cysterate, (R)-2-Amino-3-sulfopropanoic acid, (S)-2-Amino-3-sulfopropanoic acid, [13100-82-8] [RN], 207-861-3 [EINECS], 2-Amino-3-sulfopropionic acid, 35554-98-4 [RN], 3-Sulfoalanine, (L)-, 3-sulfoalanine|alanine, 3-sulfo-, Alanine, 3-sulfo-, L-, C-9550, Cepteic acid, Cipteic acid, cysteate, cysteinate, cysteine sulfonic acid, CYSTEINESULFONIC ACID, Cysteinic acid, Cysteins??ure, Cysteric acid, DL-CYSTEICACID, L-Alanine, 3-sulfo- [ACD/Index Name], L-Cysteate, L-Cysteic acid, 8, MFCD00007524, MFCD00065088 [MDL number], β-Sulfoalanine

3-sulfoalanine is an organic compound with the formula HO3SCH2CH(NH2)CO2H.
At near-neutral pH, 3-sulfoalanine exists in the form −O3SCH2CH(NH3+)CO2−.

3-sulfoalanine belongs to the class of organic compounds known as alpha amino acids, characterized by the amino group being attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
3-sulfoalanine is generated by the oxidation of cysteine, where the thiol group is fully oxidized to a sulfonic acid/sulfonate group.
3-sulfoalanine is further metabolized via 3-sulfolactate, which is subsequently converted to pyruvate and sulfite/bisulfite through enzymatic reactions catalyzed by L-3-sulfoalanine sulfo-lyase.

3-sulfoalanine serves as a biosynthetic precursor to taurine in microalgae, whereas in animals, most taurine is derived from cysteine sulfinate.
3-sulfoalanine plays a significant role in taurine and hypotaurine metabolism in humans, involving its conversion into taurine through interactions with enzymes such as cysteine sulfinic acid decarboxylase and glutamate decarboxylase 1.
3-sulfoalanine and cysteine sulfinic acid, intermediates in taurine biosynthesis in the brain, have been shown to significantly reduce [3H]taurine uptake in cultured neurons, while other compounds like cysteine, isethionic acid, cysteamine, and cystamine do not affect taurine transport.

3-sulfoalanine exists in all living species, ranging from bacteria to humans.
3-sulfoalanine has been identified as a metabolite in various organisms, including Escherichia coli (strain K12, MG1655), Phaseolus vulgaris (common bean), and humans.

3-sulfoalanine is naturally present in specific contexts, such as the outer part of sheep fleece exposed to light and weather and as a product isolated from human hair oxidized with permanganate.
Furthermore, Fmoc-L-3-sulfoalanine, a protected derivative of 3-sulfoalanine, has potential applications in proteomics and solid-phase peptide synthesis, serving as an unusual amino acid analog useful in deconvoluting protein structure and function.

3-sulfoalanine is also of interest due to its chemical reactivity.
3-sulfoalanine is an amino sulfonic acid, a sulfonic acid analogue of cysteine, and a non-proteinogenic alpha-amino acid.

3-sulfoalanine's oxidation products include mixed disulfides and disulfide cross-links within or between molecules, facilitated by transition metals like Cu2+ and Fe3+.
These properties, along with its broad biological relevance, make 3-sulfoalanine a compound of significant interest across various scientific disciplines.

3-sulfoalanine can be readily oxidized, where the main degradation products are mixed disulfides within one molecule, disulfide cross-links between molecules, and sulfenic, sulfinic, and 3-sulfoalanine.
Transition metals such as Cu2+ and Fe3+ can catalyze the formation of disulfide bonds.

As an example, human fibroblast growth factor (FGF-1) forms dimers as the result of intermolecular disulfides by copper-catalyzed oxidation.
These metal-catalyzed reactions generally can occur without a neighboring thiol group.

In the absence of transition metals the formation of new intramolecular or intermolecular disulfide bridges generally requires a nearby free thiol group that breaks apart the existing native disulfide bridge and then the free thiol can reoxidize to form the disulfide bridge.
Since this reaction requires a free thiol anion (pKa is ∼9) an increase in the solution pH will result in an increase in formation of mixed disulfide.

However, the pKa values for 3-sulfoalanine can vary depending on the proximity of other ionizing groups in the tertiary structure.
These interactions are primarily electrostatic in nature and since the ionization of these neighboring groups changes with the pH the pKa values of the 3-sulfoalanine residues will be a function of pH.

As an example, the thiol pKa in papain for the active site Cys 25 has been estimated to be 4.1 at pH 6 and 8.4 at pH 9.
This observation suggests that at pH 6 there is a His residue with positive charge in close proximity to 3-sulfoalanine 25, whereas at pH 9 the electrostatic interactions are dominated by close negatively charged residues such as Asp or Glu residues.

The effects of local electrostatic environments on thiol pKa values and disulfide exchange have been discussed by Snyder, Cennerazzo, Karalis, and Field (1981).
Ion pairing with His residues has also been proposed for the decrease in the Cys pKa values.

3-sulfoalanine has been used to couple to hydrophobic labels like Cyanine and Rhodamine dyes and other hydrophobic residues to increase their solubility in water.
As di- or tripeptide a further increase of hydrophilicity can be achieved

3-sulfoalanine can be coupled in SPPS by standard phosphoniumor uranium-based coupling reagents.
In high throughput technologies for DNA sequencing and genomics charge-modified dye-labelled
dideoxynucleoside-5’-triphosphates were synthesized for “direct-load” applications in DNA.

L-Cysteine and L-3-sulfoalanine were synthesized by paired eletrolysis method.
A high purity over 98% and high yield over 90% of both products were gained.

When current density was 7 A/dm2 and concentration of L-cysteine was 0.6 mol/dm3, the highest current efficiency of anode and cathode was achieved.
Total current efficiency was over 180%.

The cyclic voltammetry behaviors of hydrobromic acid and cystine showed that a typical EC reaction took place in the anodic cell.
The anode reaction and successive chemical reaction accelerated each other to get a high speed and current efficiency.

L-3-sulfoalanine is the L-enantiomer of 3-sulfoalanine.
3-sulfoalanine has a role as an Escherichia coli metabolite and a human metabolite.

3-sulfoalanine is a 3-sulfoalanine, an amino sulfonic acid, a L-alanine derivative, a L-cysteine derivative and a non-proteinogenic L-alpha-amino acid.
3-sulfoalanine is a conjugate acid of a L-3-sulfoalanine(1-).

L-3-sulfoalanine is a beta-sulfoalanine.
3-sulfoalanine is an amino acid with a C-terminal sulfonic acid group which has been isolated from human hair oxidized with permanganate.
3-sulfoalanine occurs normally in the outer part of the sheep's fleece, where the wool is exposed to light and weather.

Uses of 3-sulfoalanine:
An amino acid with a C-terminal sulfonic acid group which has been isolated from human hair oxidized with permanganate.
3-sulfoalanine occurs normally in the outer part of the sheep's fleece, where the wool is exposed to light and weather.

Application of 3-sulfoalanine:
Internal standard for amino acid analysis.

Biochem/physiol Actions of 3-sulfoalanine:
L-3-sulfoalanine is a sulfur containing aspartate analogue that may be used as a competitive inhibitor of the bacterial aspartate: alanine antiporter (AspT) exchange of aspartate and in other aspartate biological systems.
L-3-sulfoalanine is used in monomeric surfactant development.

L-3-sulfoalanine is an oxidation product of Cysteine.
L-3-sulfoalanine, an analogue of cysteine sulfinic acid, may be used in studies of excitatory amino acids in the brain, such as those that bind to cysteine sulfinic acid receptors.
L-3-sulfoalanine is a useful agonist at several rat metabotropic glutamate receptors (mGluRs).

Pharmacology and Biochemistry of 3-sulfoalanine:

Human Metabolite Information:

Cellular Locations:
Mitochondria

Handling and storage of 3-sulfoalanine:

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.
Dry.

Storage class:
Storage class (TRGS 510): 11: Combustible Solids

Stability and reactivity of 3-sulfoalanine:

Reactivity:

The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.

Chemical stability:
3-sulfoalanine is chemically stable under standard ambient conditions (room temperature).

Possibility of hazardous reactions:
No data available

Conditions to avoid:
no information available

Incompatible materials:
Strong oxidizing agents

First aid measures of 3-sulfoalanine:

If inhaled:

After inhalation:
Fresh air.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.

In case of eye contact:

After eye contact:
Rinse out with plenty of water.
Remove contact lenses.

If swallowed:

After swallowing:
Make victim drink water (two glasses at most).
Consult doctor if feeling unwell.

Firefighting measures of 3-sulfoalanine:

Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder

Unsuitable extinguishing media:
For 3-sulfoalanine no limitations of extinguishing agents are given.

Special hazards arising from 3-sulfoalanine:
Carbon oxides
Nitrogen oxides (NOx)
Sulfur oxides
Combustible.

Development of hazardous combustion gases or vapours possible in the event of fire.

Advice for firefighters:
In the event of fire, wear self-contained breathing apparatus.

Further information:
Suppress (knock down) gases/vapors/mists with a water spray jet.
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Accidental release measures of 3-sulfoalanine:

Personal precautions, protective equipment and emergency procedures:

Advice for non-emergency personnel:
Avoid inhalation of dusts.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains. Collect, bind, and pump off spills.
Observe possible material restrictions.

Take up dry.
Dispose of properly.

Clean up affected area.
Avoid generation of dusts.

Identifiers of 3-sulfoalanine:
CAS Number:
13100-82-8 (D/L)
35554-98-4 (D)
498-40-8 (L)

ChEBI: CHEBI:17285
ChemSpider: 65718
DrugBank: DB03661
ECHA InfoCard: 100.265.539
EC Number: 207-861-3
MeSH: Cysteic+acid
PubChem CID: 25701

UNII:
A3OGP4C37W (D/L)
YWB11Z1XEI (D)
M6W2DJ6N5K (L)

CompTox Dashboard (EPA): DTXSID40862048
InChI: InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
Key: XVOYSCVBGLVSOL-REOHCLBHSA-N
InChI=1/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
SMILES: C(C(C(=O)O)N)S(=O)(=O)O

Synonym(s): (R)-2-Amino-3-sulfopropionic acid
Linear Formula: HO3SCH2CH(NH2)CO2H·H2O
CAS Number: 23537-25-9
Molecular Weight: 187.17
Beilstein: 3714036
MDL number: MFCD00149544
PubChem Substance ID: 24858207
NACRES: NA.26

CAS: 498-40-8
Molecular Formula: C3H7NO5S
Molecular Weight (g/mol): 169.15
MDL Number: MFCD00007524
InChI Key: XVOYSCVBGLVSOL-UHFFFAOYNA-N
PubChem CID: 72886
ChEBI: CHEBI:17285
IUPAC Name: 2-amino-3-sulfopropanoic acid
SMILES: NC(CS(O)(=O)=O)C(O)=O

Properties of 3-sulfoalanine:
Chemical formula: C3H7NO5S
Molar mass: 169.15 g·mol−1
Appearance: White crystals or powder
Melting point: Decomposes around 272 °C
Solubility in water: Soluble

Quality Level: 200
Assay: ≥99.0% (T)
form: powder or crystals
optical activity: [α]20/D +7.5±0.5°, c = 5% in H2O
technique(s): LC/MS: suitable
color: white to faint yellow
mp: 267 °C (dec.) (lit.)
solubility: H2O: soluble
application(s): peptide synthesis
SMILES string: [H]O[H].N[C@@H](CS(O)(=O)=O)C(O)=O
InChI: 1S/C3H7NO5S.H2O/c4-2(3(5)6)1-10(7,8)9;/h2H,1,4H2,(H,5,6)(H,7,8,9);1H2/t2-;/m0./s1
InChI key: PCPIXZZGBZWHJO-DKWTVANSSA-N

Molecular Weight: 169.16 g/mol
XLogP3-AA: -4.5
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 3
Exact Mass: 169.00449350 g/mol
Monoisotopic Mass: 169.00449350 g/mol
Topological Polar Surface Area: 126Å²
Heavy Atom Count: 10
Complexity: 214
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of 3-sulfoalanine:
Color: White
Quantity: 1 g
Formula Weight: 169.15
Percent Purity: ≥98.0% (T)
Physical Form: Crystalline Powder
Chemical Name or Material: L-Cysteic Acid

Related Products of 3-sulfoalanine:
(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol
(R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxylic Acid Methyl Ester
[2R-[2a,6a,7b(R*)]]-7-[[[[(1,1-Dimethylethoxy)carbonyl]amino]phenylacetyl]amino]-3-methylene-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic Acid 5-Oxide
(S)-4',7-Dimethyl Equol
(3a'R,4'S,5'S,6a'S)-5'-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]hexahydro-N-[(1R)-2-hydroxy-1-phenylethyl]-5,5-dimethyl-spiro[1,3-dioxane-2,2'(1'H)-pentalene]-4'-carboxamide

Names of 3-sulfoalanine:

IUPAC name:
(R)-2-Amino-3-sulfopropanoic acid

Regulatory process names:
L-cysteic acid
L-cysteic acid

Other names:
3-Sulfo-l-alanine

Other identifiers:
498-40-8