S-Acetamidomethyl-L-cysteine hydrochloride
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S-Acetamidomethyl-L-cysteine hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-004192
CAS number
28798-28-9
Molecular Formula
C6H12N2O3S·HCl
Molecular Weight
228.70
S-Acetamidomethyl-L-cysteine hydrochloride
IUPAC Name
(2R)-3-(acetamidomethylsulfanyl)-2-aminopropanoic acid;hydrochloride
Synonyms
L-Cys(Acm)-OH HCl; (2R)-2-Amino-3-[(Acetamidomethyl)Sulfanyl]Propanoic Acid Hydrochloride
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
~165 °C (dec.)
Boiling Point
470.8°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C6H12N2O3S.ClH/c1-4(9)8-3-12-2-5(7)6(10)11;/h5H,2-3,7H2,1H3,(H,8,9)(H,10,11);1H/t5-;/m0./s1
InChI Key
SZWPOAKLKGUXDD-JEDNCBNOSA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)O)N.Cl

S-Acetamidomethyl-L-cysteine hydrochloride is an amino acid derivative commonly used in various biochemical and pharmaceutical applications. Here are some key applications of S-Acetamidomethyl-L-cysteine hydrochloride:

Peptide Synthesis: S-Acetamidomethyl-L-cysteine hydrochloride is frequently used as a building block in peptide synthesis. Its unique properties help in protecting cysteine residues during the assembly of peptides, ensuring stability and preventing unwanted side reactions. This is crucial for the successful production of complex peptide chains used in research and therapeutics.

Protein Modification: In protein chemistry, S-Acetamidomethyl-L-cysteine hydrochloride serves as a protective group for cysteine residues. It helps in preventing the oxidation of thiol groups during protein manipulation processes. This protective role is essential for maintaining the integrity of proteins during purification and structural studies.

Drug Development: S-Acetamidomethyl-L-cysteine hydrochloride can be utilized in the development of small molecule drugs and therapeutic peptides. Its selective reactivity with cysteine residues makes it a valuable tool for the design and optimization of drug candidates. Researchers can modify peptides to improve their stability, bioavailability, and efficacy using this compound.

Antioxidant Research: In antioxidant studies, S-Acetamidomethyl-L-cysteine hydrochloride is used to probe the role of cysteine residues in protein function and stability. By selectively modifying cysteine residues, scientists can investigate how these modifications affect the antioxidant properties of proteins. This research is important for understanding cellular defense mechanisms against oxidative stress.

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