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Application Area

D-Cysteine ethyl ester hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Pharmaceutical intermediates.

Category

D-Amino Acids

Catalog number

BAT-001608

CAS number

75521-14-1

Molecular Formula

C5H11NO2S·HCl

Molecular Weight

185.70

IUPAC Name

ethyl (2S)-2-amino-3-sulfanylpropanoate;hydrochloride

Synonyms

D-Cys-OEt HCl

Appearance

White powder

Purity

≥ 99% (HPLC)

Melting Point

124-126°C

Storage

Store at 2-8 °C

InChI

InChI=1S/C5H11NO2S.ClH/c1-2-8-5(7)4(6)3-9;/h4,9H,2-3,6H2,1H3;1H/t4-;/m1./s1

InChI Key

JFKJWWJOCJHMGV-PGMHMLKASA-N

Canonical SMILES

CCOC(=O)C(CS)N.Cl

D-Cysteine ethyl ester hydrochloride, a derivative of the amino acid D-cysteine, boasts a myriad of applications in bioscience. Here are four key applications:

Chemical Synthesis: Widely employed in peptide and protein synthesis, D-Cysteine ethyl ester hydrochloride’s ester form heightens its reactivity, facilitating the formation of peptide bonds in chemical reactions. This compound plays a pivotal role in generating intricate biomolecules for pharmaceutical and research endeavors, orchestrating the creation of essential structures for diverse applications.

Pharmaceutical Formulations: A cornerstone in drug development, this compound serves as a fundamental building block for pharmaceutical drugs, especially those necessitating cysteine-related architectures. Acting as a precursor in drug synthesis, it contributes to the production of medications endowed with antioxidant properties. Leveraging its reactivity and solubility, researchers craft robust and efficacious pharmaceutical formulations, driving innovation in therapeutic advancements.

Biochemical Research: Valued for its implications in redox biology and thiol-based biochemical processes, D-Cysteine ethyl ester hydrochloride plays a pivotal role in elucidating the intricacies of intracellular phenomena. Its ester form enables seamless penetration of cell membranes, empowering researchers to delve into the realm of oxidative stress and antioxidant therapies. This application stands as a cornerstone in unraveling cellular complexities and advancing therapeutic modalities.

Analytical Chemistry: In the realm of analytical sciences, D-Cysteine ethyl ester hydrochloride finds utility in sample derivatization for enhanced detection and quantification purposes. Interacting with diverse analytes, it amplifies their detectability in chromatographic and spectroscopic analyses, bolstering the precision and sensitivity of analytical assays. This compound serves as an indispensable tool in research and quality control laboratories, refining analytical methodologies and fostering scientific rigor.

1. Vibrational and structural behavior of (L)-cysteine ethyl ester hydrochloride in the solid state and in aqueous solution

M E Defonsi Lestard, S B Díaz, M Puiatti, G A Echeverría, O E Piro, A B Pierini, A Ben Altabef, M E Tuttolomondo J Phys Chem A. 2013 Dec 27;117(51):14243-52. doi: 10.1021/jp409252d. Epub 2013 Dec 16.

The aim of this work is to evaluate the vibrational and structural properties of l-cysteine ethyl ester hydrochloride (CE), and its electronic behavior mainly in relation to the action of the thiol and amine groups at different degrees of solvation. The crystal structure of CE was determined at room temperature by X-ray diffraction methods. Infrared and Raman spectra were collected to compare the behavior of different functional groups in the molecule, both in the solid phase and in aqueous solution. Its UV and circular dichroism spectra were also measured in aqueous solution. The influence of an aqueous environment on the CE spectra was simulated by means of implicit (polarizable continuum model) and explicit (molecular dynamics, solute-solvent clusters) methods. Calculations in explicit and continuous solvent are of interest to explain the behavior of bioavailable sites in this medium. The study was completed by natural bond orbital analysis to determine the presence of hyperconjugative interactions.

3. Preparation and properties of S-nitroso-L-cysteine ethyl ester, an intracellular nitrosating agent

R Clancy, A I Cederbaum, D A Stoyanovsky J Med Chem. 2001 Jun 7;44(12):2035-8. doi: 10.1021/jm000463f.

In this report, a protocol for the preparation of the hydrochloride of S-nitroso-L-cysteine ethyl ester (SNCEE.HCl; 2) is presented. The synthesis of 2 has been targeted because S-nitroso-L-cysteine (SNC; 2b), which is extensively used for trans-S-nitrosation of thiol-containing proteins, has a limited ability of crossing cellular membranes. The nitrosothiol 2 was prepared via direct S-nitrosation of the hydrochloride of L-cysteine ethyl ester (CEE.HCl; 1a) with ethyl nitrite. 2 is relatively stable in crystal form and when neutralized to SNCEE (2a) in aqueous solutions treated with chelators of metal ions. Traces of metal ions, however, triggered the decomposition of 2a to nitric oxide and a S-centered radical, which were detected by ESR spectrometry. In contrast to 2b, 2a is a lipophilic compound that was taken up by human neutrophils. The latter process was paralleled by inhibition of the NADPH oxidase-dependent generation of superoxide anion radicals, presumably via reaction(s) of intracellular trans-S-nitrosation. Intracellular accumulation of S-nitrosothiols was observed with 2a but not with 2b. It is expected that the use of 2a will be advantageous when intracellular reactions of trans-S-nitrosation are to be studied.