D-Cysteine ethyl ester hydrochloride
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D-Cysteine ethyl ester hydrochloride

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Pharmaceutical intermediates.

Category
D-Amino Acids
Catalog number
BAT-001608
CAS number
75521-14-1
Molecular Formula
C5H11NO2S·HCl
Molecular Weight
185.70
D-Cysteine ethyl ester hydrochloride
IUPAC Name
ethyl (2S)-2-amino-3-sulfanylpropanoate;hydrochloride
Synonyms
D-Cys-OEt HCl
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
124-126ºC
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
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.
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