S-Acetamidomethyl-D-cysteine hydrochloride
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S-Acetamidomethyl-D-cysteine hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-003567
CAS number
200352-41-6
Molecular Formula
C6H12N2O3S·HCl
Molecular Weight
228.70
S-Acetamidomethyl-D-cysteine hydrochloride
IUPAC Name
(2S)-3-(acetamidomethylsulfanyl)-2-aminopropanoic acid;hydrochloride
Synonyms
(S)-3-((Acetamidomethyl)Thio)-2-Aminopropanoic Acid Hydrochloride
Appearance
White to off-white powder
Purity
≥ 98%
Melting Point
150-183 °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-;/m1./s1
InChI Key
SZWPOAKLKGUXDD-NUBCRITNSA-N
Canonical SMILES
CC(=O)NCSCC(C(=O)O)N.Cl

S-Acetamidomethyl-D-cysteine hydrochloride is a chemical compound with various applications, especially in the bioscience and pharmaceutical fields. Here are some key applications of S-Acetamidomethyl-D-cysteine hydrochloride:

Peptide Synthesis: S-Acetamidomethyl-D-cysteine hydrochloride is commonly used in peptide synthesis as a protecting group for cysteine residues. The acetamidomethyl group prevents the thiol group of cysteine from oxidizing and forming disulfide bonds prematurely. This ensures the proper folding and function of synthetic peptides, crucial for studies in protein structure and drug development.

Bioconjugation: This compound is often used in bioconjugation processes, where it serves as a linker molecule to join two different biomolecules. S-Acetamidomethyl-D-cysteine hydrochloride can help in attaching peptides or proteins to other molecules, such as drugs, fluorescent markers, or solid supports. This facilitates the creation of targeted therapeutic agents and diagnostic tools.

Protein Engineering: In protein engineering, S-Acetamidomethyl-D-cysteine hydrochloride is used to introduce specific cysteine modifications. This allows researchers to study the role of cysteine in protein function and stability by creating modified proteins with controlled thiol group reactivity. Such modifications are important in the design of proteins with novel properties for industrial and biomedical applications.

Antibody-Drug Conjugates (ADCs): S-Acetamidomethyl-D-cysteine hydrochloride can be used in the development of antibody-drug conjugates. By protecting the cysteine residues, it enables the precise and selective conjugation of drugs to antibodies. This is pivotal for creating targeted cancer therapies that deliver cytotoxic drugs specifically to tumor cells, thereby minimizing side effects and increasing treatment efficacy.

1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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