CAS 2002-22-4

(αS)-α-Amino-2,3-dihydro-2-thioxo-1H-imidazole-4-propanoic acid

Description:

(αS)-α-Amino-2,3-dihydro-2-thioxo-1H-imidazole-4-propanoic acid, commonly referred to as a thiazolidine derivative, is an amino acid analog characterized by its unique imidazole ring structure and thioxo functional group. This compound features a chiral center, which contributes to its stereochemistry, specifically the (αS) configuration. It is typically a white to off-white crystalline solid, soluble in water and polar organic solvents, making it suitable for various biochemical applications. The presence of the thioxo group imparts distinct reactivity, allowing it to participate in diverse chemical reactions, including nucleophilic attacks and coordination with metal ions. This compound is of interest in pharmaceutical research, particularly in the development of novel therapeutics due to its potential biological activity. Its properties, such as melting point, boiling point, and specific reactivity, can vary based on environmental conditions and the presence of other substances. Overall, (αS)-α-Amino-2,3-dihydro-2-thioxo-1H-imidazole-4-propanoic acid represents a fascinating area of study within organic and medicinal chemistry.

Formula: C₆H₉N₃O₂S

InChI: InChI=1S/C6H9N3O2S/c7-4(5(10)11)1-3-2-8-6(12)9-3/h2,4H,1,7H2,(H,10,11)(H2,8,9,12)/t4-/m0/s1

InChI key: InChIKey=FVNKWWBXNSNIAR-BYPYZUCNSA-N

SMILES: C([C@@H](C(O)=O)N)C1=CNC(=S)N1

Synonyms:

• (2S)-2-Azaniumyl-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)propanoate
• (S)-2-Amino-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)propanoic acid
• (αS)-α-Amino-2,3-dihydro-2-thioxo-1H-imidazole-4-propanoic acid
• 1H-Imidazole-4-propanoic acid, α-amino-2,3-dihydro-2-thioxo-, (S)-
• 1H-Imidazole-4-propanoic acid, α-amino-2,3-dihydro-2-thioxo-, (αS)-
• 2-Mercapto-<span class="text-smallcaps">L</span>-histidine
• 2-Mercapto-L-histidine
• 2-Mercaptohistidine
• 3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-L-alanine
• <span class="text-smallcaps">L</span>-2-Mercaptohistidine
• <span class="text-smallcaps">L</span>-2-Thiolhistidine
• <span class="text-smallcaps">L</span>-2-Thioxohistidine
• <span class="text-smallcaps">L</span>-Thiohistidine
• Histidine, 2-mercapto-, <span class="text-smallcaps">L</span>-
• L-2-Mercaptohistidine

H-2-Mercapto-His-OH

CAS: 2002-22-4

Key intermediate in the synthesis of the naturally occurring amino acid L-(+)-ergothioneine and analogs.

Formula: C₆H₉N₃O₂S

Purity: ≥ 98%

Color and Shape: Yellowish Powder

Molecular weight: 187.22

Ref: 01-4014107

1H-Imidazole-4-propanoic acid, α-amino-2,3-dihydro-2-thioxo-, (αS)-

CAS: 2002-22-4

Formula: C₆H₉N₃O₂S

Purity: 95%

Color and Shape: Solid

Molecular weight: 187.2196

Ref: IN-DA002CM6

(S)-2-Amino-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)propanoic acid

CAS: 2002-22-4

(S)-2-Amino-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)propanoic acid

Purity: 95%

Molecular weight: 187.22g/mol

Ref: 54-OR1072588

2-Mercapto-L-histidine

CAS: 2002-22-4

2-Mercapto-L-histidine is a dietary amino acid that has been shown to be an effective inhibitor of opportunistic fungal growth in vitro. It has been shown to have a second-order rate constant of 0.0037 s−1, which is the same as lysine and arginine. This compound also inhibits the growth of fungi by competing with tryptophan for binding sites on the enzyme histidine ammonia-lyase. 2-Mercapto-L-histidine can also react with nucleophiles such as divalent cations and form covalent bonds, which may lead to its antimicrobial activity against Gram-positive bacteria. 2-Mercapto-L-histidine is not active against Gram negative bacteria or yeast due to structural differences in their cell walls.
2-Mercapto-L-histidine has been shown to inhibit glucose metabolism and plasma glucose levels in vitro, but it does not affect insulin secretion or

Formula: C₆H₉N₃O₂S

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 187.22 g/mol

Ref: 3D-FM25093

2-Mercapto-L-histidine

Controlled Product

CAS: 2002-22-4

Applications An intermediate in the formation of L-egothioneine, a natural amino acid ubiquitously present in cells and tissues of most plants and mammalian species. In humans, L-ergothioneine is found in red blood cells, liver, kidney, brain, seminal fluid, and cataract-free lenses at concentrations ranging from 100 uM to 2 mM. L-ergothioneine is exclusively biosynthesized in fungi and mycobacteria. Hence, humans assimilate it through dietary intake.L-ergothioneine has been proven to act as an antioxidant in vivo and to afford protection from g and UV radiation as well as from singlet oxygen in vivo. Recently, it has been shown that L-ergothioneine protects isolated perfused heart against the deleterious effect of post-ischemic reperfusion.The intermediate, 2-mercaptohistine has been used for the
References Makinen, K.K., et al.: Eur. J. Biochem., 123, 171 (1982), Howard, R.J., et al.: Biochem. Pharmacol., 35, 1589 (1986),

Formula: C₆H₉N₃O₂S

Color and Shape: Neat

Molecular weight: 187.22

Ref: TR-M253000