349-46-2

Usage

Uses

Used in Pharmaceutical Industry:
D-Cystine is used as an additive for increasing the rate of fertilization of mouse oocytes. This application is particularly relevant in the field of reproductive medicine and assisted reproductive technologies, where improving the success rate of fertilization is of great importance.
Additionally, D-Cystine may have potential applications in other areas of the pharmaceutical industry, such as in the development of drugs targeting specific biological processes or as a component in the synthesis of complex molecules. However, further research and development would be required to explore these possibilities.

InChI:InChI=1/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m1/s1

Upstream product

• 921-01-7 rac-cysteine 
• 52-90-4 L-Cysteine 
• 505-73-7 disulfanediyldiacetic acid 
• 56-89-3 L-cystine 
• 69-78-3 5,5'-dithiobis-(2-nitrobenzoic acid) 
• 16136-29-1 2-Amino-2-carboxy-ethanethiol anion 
• 90792-25-9 anthraquinone-2,6-disulfonate 
• 51209-75-7 S-nitroso-cysteine 
• 7647-01-0 hydrogenchloride 
• 23052-19-9 di-γ-glutamyl-cystine 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 7664-41-7 ammonia 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 2150-55-2 2-amino-⁽²⁾-thiazoline-4-carboxylic acid 
• 74-93-1 methylthiol 
• 352-93-2 diethyl sulphide 
• 921-01-7 rac-cysteine 
• 52-90-4 L-Cysteine 
• 13100-82-8 cysteic acid 
• 51-85-4 2,2'-dithio-bis[ethylamine] 
• 75-07-0 acetaldehyde 
• 5545-17-5 N,N'-diacetyl-DL-cystine 
• 302-72-7 rac-Ala-OH 
• 107-96-0 3-mercaptopropionic acid 
• 29581-98-4 N,N'-diformyl-DL-cystine 
• 879878-64-5 NSC₁₁₄₅₃₂ 
• 6630-89-3 N,N'-bis-phenylcarbamoyl-cystine 

Relevant academic research and scientific papers

The L-cysteine/L-cystine shuttle system provides reducing equivalents to the periplasm in Escherichia coli

Intracellular thiols like L-cysteine and glutathione play a critical role in the regulation of cellular processes. Escherichia coli has multiple L-cysteine transporters, which export L-cysteine from the cytoplasm into the periplasm. However, the role of L-cysteine in the periplasm remains unknown. Here we show that an L-cysteine transporter, YdeD, is required for the tolerance of E. coli cells to hydrogen peroxide. We also present evidence that L-cystine, a product from the oxidation of L-cysteine by hydrogen peroxide, is imported back into the cytoplasm in a manner dependent on FliY, the periplasmic L-cystine-binding protein. Remarkably, this protein, which is involved in the recycling of the oxidized L-cysteine, is also found to be important for the hydrogen peroxide resistance of this organism. Furthermore, our analysis of the transcription of relevant genes revealed that the transcription of genes encoding FliY and YdeD is highly induced by hydrogen peroxide rather than by L-cysteine. These findings led us to propose that the inducible L-cysteine/L-cystine shuttle system plays an important role in oxidative stress tolerance through providing a reducing equivalent to the periplasm in E. coli.

Kinetic studies of the reaction of S-nitroso-L-cysteine with L-cysteine

Rates for the reaction between L-S-nitrosocysteine and L-cysteine were found to be first order with respect to concentrations of the two reactants in the pH range of 4.85 - 9.41. The second order rate constant was determined to be 3.10 x 10-2 M-1 s-1 at pH = 7.4 at 37 °C. Spontaneous decomposition of L-S-nitrosocysteine proceeded with the first order rate constant, 1.46 x 10-5 s-1 under the same conditions.

Peroxidase-mimicking DNAzyme modulated growth of CdS nanocrystalline structures in situ through redox reaction: Application to development of genosensors and aptasensors

This work demonstrates the use of the peroxidase-mimicking DNAzyme (peroxidase-DNAzyme) as general and inexpensive platform for development of fluorogenic assays that do not require organic fluorophores. The system is based on the affinity interaction between the peroxidase-DNAzyme bearing hairpin sequence and the analyte (DNA or low molecular weight molecule), which changes the folding of the hairpin structure and consequently the activity of peroxidase-DNAzyme. Hence, in the presence of the analyte the peroxidase-DNAzyme structure is disrupted and does not catalyze the aerobic oxidation of l-cysteine to cystine. Thus, l-cysteine is not removed from the system and the fluorescence of the assay increases due to the in situ formation of fluorescent CdS nanocrystals. The capability of the system as a platform for fluorogenic assays was demonstrated through designing model geno- and aptasensor for the detection of a tumor marker DNA and a low molecular weight analyte, adenosine 5triphosphate (ATP), respectively.

STUDIES ON 2-AZIRIDINECARBOXYLIC ACID: X. SIMPLE STEREOSPECIFIC SYNTHESIS OF OPTICALLY ACTIVE CYSTINE AND THREO-3,3 prime -DIMETHYLCYSTINE.

Results show that, compared with conventional methods the synthesis of cysteine and 3-methylcysteine by the stereospecific ring-opening reaction of aziridine with H//2S is very convenient for transforming the serine or threonine into optically pure cystine or threo-3,3 prime -dimethylcystine.

Preparation method of high-purity D-cystine

The invention discloses a preparation method of high-purity D-cystine. The preparation method comprises the following steps: hydrolyzing D-2, 2-dimethyltetrahydrothiazole-4-carboxylic acid.L-tartrate,and converting the hydrolysate, specifically, converting L-tartaric acid in the hydrolysate into Lentinite, which is separated out as a precipitate; then, before the filtrate is oxidized, the pH value of the filtrate is firstly reduced so that introduction of more impurities in the oxidation process is reduced, and high-purity and high-yield D-cysteine is obtained; the whole preparation method issimple in production process, safe in used raw materials, easy to control, free of high-temperature and high-pressure reaction, low in equipment investment and easy to produce and operate.

Electropolymerization of cobalt tetraamino-phthalocyanine at reduced graphene oxide for electrochemical determination of cysteine and hydrazine

We describe a simple and elegant electropolymerization method to prepare highly stable tetraamino functionalized cobalt phthalocyanine (pTACoPc) at electrochemically reduced graphene oxide (RGO). The described method efficiently bridges the excellent physicochemical properties of RGO with the rich redox chemistry of TACoPc. Graphene oxide was electrochemically reduced to RGO at the electrode surface along with concominent electropolymerization of TACoPc. The electrochemical studies showed that RGO on pTACoP/GCE increased effective surface area, reduced charge transfer resistance and enhanced electrochemical signal. The RGO-pTACoPc film modified electrode exhibits excellent electrocatalytic ability to oxidize cysteine and hydrazine. To determine cysteine, the RGO-pTACoPc sensor displayed a linear concentration range of 50 nM to 2.0 μM, detection limit of 18.5 nM and sensitivity of 10.19 nA nM-1 cm-2. Besides, the sensor displayed a linear concentration range of 50 nM to 2.6 μM, detection limit of 10 nM and sensitivity of 1.62 nA nM-1 cm-2 to determine hydrazine. The electrocatalytic ability of RGO-pTACoPc shows better performance over other cobalt phthalocyanine derivatives. Furthermore, the described sensor exhibited long-term storage stability, good repeatability and reproducibility. The practical applicability of the sensor has been assessed in biological and water samples.

Biochemical characterisation and assessment of fibril-forming ability of collagens extracted from Bester sturgeon Huso huso × Acipenser ruthenus

Collagens purified from Bester sturgeon organs were characterised biochemically, and their fibril-forming abilities and fibril morphologies formed in vitro clarified. Yields of collagens were 2.1%, 11.9%, 0.4%, 18.1%, 0.4%, 0.8% and 0.03% (collagen dry weight/tissue wet weight) from scales, skin, muscle, swim bladder, digestive tract, notochord and snout cartilage, respectively. Using SDS-PAGE and amino acid composition analyses, collagens from scales, skin, muscle, the swim bladder and digestive tract were characterised as type I, and collagens from the notochord and snout cartilage as type II. Denaturation temperatures of the collagens, measured using circular dichroism, were 29.6, 26.8, 29.0, 32.9, 31.6 and 36.3 °C in scales, skin, muscle, swim bladder, digestive tract, and notochord, respectively. For fibril formation, swim bladder and skin collagen showed a more rapid rate of increase in turbidity, a shorter time to attain the maximum turbidity, and formed thicker fibrils compared with porcine tendon type I collagen.

Nitrite reduction mediated by the complex RuIII(EDTA)

Reported is the first example of a ruthenium(iii)-complex, Ru III(EDTA) (EDTA4- = ethylenediaminetetraacetate), that mediates O-atom transfer from nitrite to the biological thiols cysteine and glutathione, leading to the formation of [RuIII(EDTA)(NO +)]0. However, at pH below 5.0, the coordinated nitrite ion in the [RuIII(EDTA)(NO2)]2- complex undergoes proton-assisted decomposition, resulting in the formation of a [RuIII(EDTA)(NO+)]0 species. the Partner Organisations 2014.

S-aroylthiooximes: A facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics

We report the facile preparation of a family of S-aroylthiooxime (SATO) H2S donors, which are synthesized via a click reaction analogous to oxime formation between S-aroylthiohydroxylamines (SATHAs) and aldehydes or ketones. Analysis of cysteine-triggered H2S release revealed structure-dependent release kinetics with half-lives from 8-82 min by substitution of the SATHA ring. The pseudo-first-order rate constants of substituted SATOs fit standard linear free energy relationships (p = 1.05), demonstrating a significant sensitivity to electronic effects.

Synthesis of disulfides and diselenides by copper-catalyzed coupling reactions in water

A simple and efficient protocol for copper-catalyzed coupling reactions between aryl halides and elemental sulfur or selenium has been developed. A variety of disulfides and diselenides can be obtained in moderate to excellent yields up to 96%. The Royal Society of Chemistry 2013.