CAS 2002-22-4

(αS)-α-Amino-2,3-dihidro-2-tioxo-1H-imidazol-4-propanoico ácido

Descripción:

(αS)-α-Amino-2,3-dihidro-2-tioxo-1H-imidazol-4-propanoico ácido, comúnmente conocido como un derivado de tiazolidina, es un análogo de aminoácido caracterizado por su estructura única de anillo de imidazol y grupo funcional tioxo. Este compuesto presenta un centro quiral, que contribuye a su estereoquímica, específicamente la configuración (αS). Típicamente es un sólido cristalino blanco a blanco sucio, soluble en agua y solventes orgánicos polares, lo que lo hace adecuado para diversas aplicaciones bioquímicas. La presencia del grupo tioxo confiere una reactividad distinta, permitiéndole participar en diversas reacciones químicas, incluyendo ataques nucleofílicos y coordinación con iones metálicos. Este compuesto es de interés en la investigación farmacéutica, particularmente en el desarrollo de nuevos terapéuticos debido a su potencial actividad biológica. Sus propiedades, como el punto de fusión, el punto de ebullición y la reactividad específica, pueden variar según las condiciones ambientales y la presencia de otras sustancias. En general, (αS)-α-Amino-2,3-dihidro-2-tioxo-1H-imidazol-4-propanoico ácido representa un área fascinante de estudio dentro de la química orgánica y medicinal.

Fórmula: 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

Clave InChI: InChIKey=FVNKWWBXNSNIAR-BYPYZUCNSA-N

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

Sinónimos:

• (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.

Fórmula: C₆H₉N₃O₂S

Pureza: ≥ 98%

Forma y color: Yellowish Powder

Peso molecular: 187.22

Ref: 01-4014107

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

CAS: 2002-22-4

Fórmula: C₆H₉N₃O₂S

Pureza: 95%

Forma y color: Solid

Peso molecular: 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

Pureza: 95%

Peso molecular: 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

Fórmula: C₆H₉N₃O₂S

Pureza: Min. 95%

Forma y color: Powder

Peso molecular: 187.22 g/mol

Ref: 3D-FM25093

2-Mercapto-L-histidine

Producto controlado

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),

Fórmula: C₆H₉N₃O₂S

Forma y color: Neat

Peso molecular: 187.22

Ref: TR-M253000