meso-Cystine

Base Information

• Chemical Name: meso-Cystine
• CAS No.: 56-89-3
• Molecular Formula: C6H12N2O4S2
• Molecular Weight: 240.304
• Hs Code.: 2922.49 DERIVATION
• European Community (EC) Number: 200-296-3
• UNII: KQY8R188E2
• DSSTox Substance ID: DTXSID90208952
• Nikkaji Number: J14.061I
• Wikipedia: Cystine
• Wikidata: Q27282385
• NCI Thesaurus Code: C29610
• Mol file: 56-89-3.mol

Synonyms:Copper Cystinate;Cystine;L Cystine;L-Cystine

Chemical Property of meso-Cystine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: >240 °C (dec.)(lit.)
• Refractive Index: -222.5 ° (C=1, 1mol/L HCl)
• Boiling Point: 468.2 °C at 760 mmHg
• PKA: 1.0, 2.1, 8.02, 8.71(at 25℃)
• Flash Point: 237 °C
• PSA: 177.24000
• Density: 1.571 g/cm³
• LogP: 0.59220
• Storage Temp.: Store at RT.
• Solubility.: 1 M HCl: 100 mg/mL
• Water Solubility.: 0.112 g/L (25 ºC)
• XLogP3: -6.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 240.02384922
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

99%, ^*data from raw suppliers

NPHS1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(C(C(=O)O)N)SSCC(C(=O)O)N
• Isomeric SMILES: C([C@H](C(=O)O)N)SSC[C@@H](C(=O)O)N
• Recent NIPH Clinical Trials: Perioperative oral administration of Cystine and Theanine enhances recovery after thoracoscopic esophagectomy
• Structure and Properties: Cystine is a vital amino acid derived from cysteine, appearing as a white, solid substance with low solubility in water. It forms a dimeric amino acid structure through disulfide bonds (-S-S-).
• Functions and Roles: Acts as a precursor in cellular processes, including the synthesis pathways of glutathione and taurine.; Contributes to crosslinking due to its sulfur-rich nature and is a constituent of proteins such as keratin and hydrophobins.; Utilized in nutritional products, acne treatments, creams for healing cervical injuries or inflammation, and as a flour treatment agent.; Plays roles in metabolism, promoting hair growth, combating skin aging effects, aiding post-surgical healing, protecting against radiation damage, and potentially assisting in fat burning and muscle gain.
• Metabolism and Cellular Processes: Serves as a rate-limiting precursor for glutathione, a cellular antioxidant, and can act as an antioxidant itself.; Can be synthesized through de novo biosynthesis or recycled through protein degradation.; Extracellular cystine is quickly oxidized from cysteine and has a higher concentration than extracellular cysteine.; Some cancer cells can effectively take up extracellular cysteine or cystine, depending on environmental conditions.; Cystine starvation results in glutathione depletion in cells and can induce oxidative stress-induced cell death.; Pharmacologic blockade of cystine uptake induces a form of cell death termed ferroptosis, highlighting the role of cystine in cell survival under oxidative stress conditions.
• Regulation and Mechanisms: Extracellular cystine is imported into the cell through specific transporters like SLC7A11 and converted to cysteine in the cytosol.; Cystine starvation-induced downregulation of GPX4 protein is mediated by protein translation suppression rather than mRNA transcription or protein stability reduction.

Technology Process of meso-Cystine

There total 172 articles about meso-Cystine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

L-Cysteine (52-90-4) + N-(benzoylsulfide)benzamide (134861-13-5) → L-cystine (56-89-3) + benzamide (55-21-0,27208-38-4) + D-N-benzoylcysteine

Guidance literature:

In methanol; aq. phosphate buffer; at 20 ℃; pH=7.4;

DOI:10.1021/acs.jmedchem.5b01033

Reference yield: 95.0%

rac-cysteine (921-01-7,3374-22-9,4371-52-2,40143-64-4,40143-66-6,40143-69-9,52-90-4) → cysteine disulfide (56-89-3,349-46-2,923-32-0,6020-39-9,24645-67-8,35100-73-3,40143-67-7)

Guidance literature:

With nitrogen(II) oxide; In water; for 0.25h; Ambient temperature;

DOI:10.1021/jo00340a038

Reference yield: 21.0%

H-Cys(Acm)(O)-OH (75893-05-9) → L-Cysteine (52-90-4) + L-Cysteic acid (498-40-8,3024-83-7) + L-cystine (56-89-3) + S-acetamidomethyl-L-cysteine (19647-70-2)

Guidance literature:

With ammonia; sodium; for 0.00277778h; Product distribution;

upstream raw materials:

rac-cysteine

L-Cysteine

disulfanediyldiacetic acid

5,5'-dithiobis-(2-nitrobenzoic acid)

Downstream raw materials:

L-cystine dimethyl ester

N-(2,4-dinitro-phenyl)-L-cystine

N-acetylcystein

(R)-3-methyl-1,3-thiazolidine-4-carboxylic acid

Refernces

• 1、 Ukoha, Pius O.,Ujam, Oguejiofo T.,Iyun, Johnson F.,Okereke, Solomon E.O.. "Mechanism of oxidation of L-Cysteine by Tetraoxoiodate(VII) in aqueous acid medium". . p. 3777 - 3780. Retrieved 2015.
• 2、 Zen, Jyh-Myng,Senthil Kumar, Annamalai,Chen, Jyh-Cheng. "Electrocatalytic oxidation of cysteine on a nafion-ruthenium oxide pyrochlore chemically modified electrode". . p. 743 - 744. Retrieved 1999.
• 3、 Hanaki, Akira. "Kinetic Studies on the Role of Dioxygen in the Cooper-Catalyzed Autoxidation of Cysteine". . p. 831 - 837. Retrieved 1995.
• 4、 Athilakshmi, Jeyaraman,Mohan, Manikkavalli,Chand, Dillip Kumar. "Selective detection of cysteine/cystine using silver nanoparticles". . p. 427 - 430. Retrieved 2013.
• 5、 Song, Heng,Her, Ampon Sae,Raso, Fiona,Zhen, Zhibin,Huo, Yuda,Liu, Pinghua. "Cysteine oxidation reactions catalyzed by a mononuclear non-heme iron enzyme (OvoA) in ovothiol biosynthesis". . p. 2122 - 2125. Retrieved 2014.
• 6、 Nagy, Peter,Ashby, Michael T.. "Reactive sulfur species: Kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid". . p. 14082 - 14091. Retrieved 2007.
• 7、 Shih, Hsiencheng. "New Approaches to the Synthesis of Cystine Peptides Using N-Iodosuccinimide in the Construction of Disulfide Bridges". . p. 3003 - 3008. Retrieved 1993.
• 8、 Morando, Pedro J.,Borghi, Elena B.,Schteingart, Lydia M. de,Blesa, Miguel A.. "The Reaction of Cysteine with the Pentacyanonitrosylferrate(2-) Ion". . p. 435 - 440. Retrieved 1981.
• 9、 Nagy, Peter,Lemma, Kelemu,Ashby, Michael T.. "Reactive sulfur species: Kinetics and mechanisms of the reaction of cysteine thiosulfinate ester with cysteine to give cysteine sulfenic acid". . p. 8838 - 8846. Retrieved 2007.
• 10、 Zhou, Ming,Ding, Jie,Guo, Li-Ping,Shang, Qing-Kun. "Electrochemical behavior of L-cysteine and its detection at ordered mesoporous carbon-modified glassy carbon electrode". . p. 5328 - 5335. Retrieved 2007.