Acetyl-L-cystine bis-methyl ester[Disulfide bond]
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Acetyl-L-cystine bis-methyl ester[Disulfide bond]

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Category
L-Amino Acids
Catalog number
BAT-004216
CAS number
32381-28-5
Molecular Formula
C12H20N2O6S2
Molecular Weight
352.43
Acetyl-L-cystine bis-methyl ester[Disulfide bond]
IUPAC Name
methyl (2R)-2-acetamido-3-[[(2R)-2-acetamido-3-methoxy-3-oxopropyl]disulfanyl]propanoate
Synonyms
(Ac-L-Cys-OMe)2; Dimethyl diacetyl cystinate
Appearance
White powder
Purity
≥ 98% (Assay)
Density
1.285±0.06 g/cm3(Predicted)
Melting Point
77-81 °C
Boiling Point
584.5±50.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H20N2O6S2/c1-7(15)13-9(11(17)19-3)5-21-22-6-10(12(18)20-4)14-8(2)16/h9-10H,5-6H2,1-4H3,(H,13,15)(H,14,16)/t9-,10-/m0/s1
InChI Key
ZTTORBNKJFMGIM-UWVGGRQHSA-N
Canonical SMILES
CC(=O)NC(CSSCC(C(=O)OC)NC(=O)C)C(=O)OC

Acetyl-L-cystine bis-methyl ester, renowned for its distinctive disulfide bond, finds diverse applications in bioscience. Here are four key applications:

Antioxidant Research: Playing a pivotal role in antioxidant research, Acetyl-L-cystine bis-methyl ester demonstrates its prowess in modulating oxidative stress within biological systems. By replenishing intracellular glutathione levels, it plays a crucial role in shielding cells from the detrimental effects of reactive oxygen species. Researchers utilize this compound to delve into the intricate mechanisms of oxidative damage and the protective capabilities of antioxidants.

Drug Formulation: In the realm of pharmaceutical development, Acetyl-L-cystine bis-methyl ester emerges as a promising prodrug, enhancing bioavailability and metabolic stability of active pharmaceutical ingredients. Its unique chemical structure facilitates superior delivery and absorption, potentially revolutionizing the creation of more potent and enduring medications for a multitude of diseases.

Cellular Protection: Leveraging its attributes, Acetyl-L-cystine bis-methyl ester is harnessed in both in vitro and in vivo studies to safeguard cells against toxic insults. By upholding redox homeostasis and ameliorating oxidative damage, it serves as a shield for cells facing stressors like radiation, chemotherapy, or environmental toxins. This application stands as a cornerstone in unraveling cellular defense mechanisms and crafting cytoprotective therapies.

Molecular Biology: Within the realm of molecular biology, Acetyl-L-cystine bis-methyl ester serves as a versatile tool for modulating redox-sensitive signaling pathways and protein functions. With its disulfide bond structure, it interacts with cysteine residues in proteins, exerting influence over their activity and stability. This characteristic is leveraged by researchers to explore redox regulation and devise strategies for manipulating protein function in a myriad of biological assays.

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