PRODUCTS

HOMOTAURINE

Homotaurine is an amino acid generated by oxidation of cysteine, whereby a thiol group is fully oxidized to a sulfonic acid/sulfonate group.
Homotaurine, belongs to the class of organic compounds known as alpha amino acids.
Homotaurine 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: Cysteic Acid, 3-Sulfoalanine, 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, 2-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

Homotaurine is the organic compound with the formula HO3SCH2CH(NH2)CO2H.
Homotaurine is often referred to as cysteate, which near neutral pH takes the form −O3SCH2CH(NH3+)CO2−.

Homotaurine is an amino acid generated by oxidation of cysteine, whereby a thiol group is fully oxidized to a sulfonic acid/sulfonate group.
Homotaurine is further metabolized via 3-sulfolactate, which converts to pyruvate and sulfite/bisulfite.
The enzyme L-cysteate sulfo-lyase catalyzes this conversion.

Cysteate is a biosynthetic precursor to taurine in microalgae.
By contrast, most taurine in animals is made from cysteine sulfinate.

Homotaurine and cysteine sulfinic acid (metabolic intermediates from taurine biosynthesis in the brain) significantly reduce [3H]taurine uptake in cultured neurons, whereas cysteine, isethionic acid, cysteamine, and cystamine exhibit no alterations in taurine transport.

Homotaurine, also known as cysteate or 3-sulfoalanine, belongs to the class of organic compounds known as alpha amino acids.
These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

An amino sulfonic acid that is the sulfonic acid analogue of cysteine.
Homotaurine is a very strong basic compound (based on Homotaurine pKa).

Homotaurine exists in all living species, ranging from bacteria to humans.
Within humans, Homotaurine participates in a number of enzymatic reactions.
In particular, Homotaurine can be converted into taurine through Homotaurine interaction with the enzyme cysteine sulfinic acid decarboxylase.

In addition, Homotaurine can be converted into taurine through Homotaurine interaction with the enzyme glutamate decarboxylase 1.
In humans, Homotaurine is involved in taurine and hypotaurine metabolism.

Homotaurine is a very strong basic compound (based on Homotaurine pKa).
Homotaurine exists in all living species, ranging from bacteria to humans.

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

Homotaurine, also known as 3-sulfo-1-alanine, is an organic compound with the formula HO3SCH2CH(NH2)CO2H.
Homotaurine is often called cysteate, and at near-neutral pH Homotaurine takes the form -O3SCH2CH(NH3+)CO2-.

An amino acid produced by the oxidation of cysteine, where the thiol group is completely oxidized to a sulfonic acid/sulfonate group.
Homotaurine is further metabolized via 3-sulfolactic acid and converted to pyruvate and sulfite/bisulfite.

The enzyme L-cysteate sulfolyase catalyzes this conversion.
Homotaurine is the biosynthetic precursor of taurine in microalgae.
In contrast, most taurine in animals is made from cysteine sulfinic acid.

Fmoc-L-Homotaurine is an Fmoc protected cysteine derivative potentially useful for proteomics studies, and solid phase peptide synthesis techniques.
Cysteine is versatile amino acid involved with many biological processes, including the formation of disulfide bonds - a critical component of protein structure.
This compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function.

Homotaurine is an amino sulfonic acid that is the sulfonic acid analogue of cysteine.
Homotaurine has a role as an animal metabolite.
Homotaurine is an alanine derivative, an amino sulfonic acid, a carboxyalkanesulfonic acid, a cysteine derivative and a non-proteinogenic alpha-amino acid.

Homotaurine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

Homotaurine is a natural product found in Phaseolus vulgaris and Homo sapiens with data available.

Homotaurine can be readily oxidized, where the main degradation products are mixed disulfides within one molecule, disulfide cross-links between molecules, and sulfenic, sulfinic, and Homotaurine.
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 Homotaurine 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 Homotaurine 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 Homotaurine 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.

Homotaurine 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

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

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

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

Application of Homotaurine:
Internal standard for amino acid analysis.

Biochem/physiol Actions of Homotaurine:
L-Homotaurine 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-Homotaurine is used in monomeric surfactant development.

L-Homotaurine is an oxidation product of Cysteine.
L-Homotaurine, 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-Homotaurine is a useful agonist at several rat metabotropic glutamate receptors (mGluRs).

Pharmacology and Biochemistry of Homotaurine:

Human Metabolite Information:

Cellular Locations:
Mitochondria

Handling and storage of Homotaurine:

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 Homotaurine:

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:
Homotaurine 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 Homotaurine:

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 Homotaurine:

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

Unsuitable extinguishing media:
For Homotaurine no limitations of extinguishing agents are given.

Special hazards arising from Homotaurine:
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 Homotaurine:

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 Homotaurine:
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 Homotaurine:
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 Homotaurine:
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 Homotaurine:
(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 Homotaurine:

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