L-Selenocystine

Base Information

• Chemical Name: L-Selenocystine
• CAS No.: 29621-88-3
• Molecular Formula: C₆H₁₂N₂O₄Se₂
• Molecular Weight: 334.092
• Hs Code.: 29319090
• European Community (EC) Number: 608-382-6
• UNII: 261B157KR8,493154PTZ7
• DSSTox Substance ID: DTXSID001044310
• Nikkaji Number: J14.789C
• Wikidata: Q27254027
• Metabolomics Workbench ID: 68405
• Mol file: 29621-88-3.mol

Synonyms:L-Selenocystine;29621-88-3;Selenocystine, L-;Seleno-L-cystine;L-3,3'-Diselenodialanine;Alanine, 3,3'-diselenodi-, L-;C6H12N2O4Se2;L-Selenocystine monohydrate;261B157KR8;(2R,2'R)-3,3'-diselanediylbis(2-aminopropanoic acid);3,3'-Diselenobis[L-alanine];2-Amino-3-(((R)-2-amino-2-carboxyethyl)diselanyl)propanoic acid;3,3'-DISELENOBIS(L-ALANINE);L-Alanine,3,3'-diselenobis-;C6-H12-N2-O4-Se2;Seleno-L-cystine, 95%;selenocystine, (L)-isomer;SCHEMBL160609;L-Alanine, 3,3'-diselenobis-;UNII-261B157KR8;DTXSID001044310;MFCD00800971;AKOS015915762;493154PTZ7;DL-ALANINE, 3,3'-DISELENOBIS-;LS-16101;SELENOCYSTINE, (R,R-(+/-)-)-;HY-129960;CS-0108886;S0900;C05704;(R,R)-3,3'-Diselenobis(2-aminopropionic Acid);(R,R)-3,3'-Diseleno-bis(2-aminopropionic acid);J-017582;Q27254027;(2R)-2-amino-3-[[(2R)-2-amino-2-carboxy-ethyl]diselanyl]propanoic acid

Chemical Property of L-Selenocystine

Chemical Property:

• Melting Point: 224.5-229.5 °C(lit.)
• Boiling Point: 538.3°Cat760mmHg
• PKA: 1.69±0.10(Predicted)
• Flash Point: 279.3°C
• PSA: 126.64000
• Density: g/cm³
• LogP: -0.62920
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 335.91275
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-Selenocystine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)O)N)[Se][Se]CC(C(=O)O)N
• Isomeric SMILES: C([C@@H](C(=O)O)N)[Se][Se]C[C@@H](C(=O)O)N
• Description: L-Selenocystine is a diselenide-bridged amino acid that may be confused with selenocysteine (Sec), which is a rare amino acid featuring a single selenium atom. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. This compound can be reduced by low molecular thiols and disulfide reductases to Sec. It is reduced to Sec by mammalian thioredoxin reductase (apparent Km = 6.0 μM), and this property can be used to assay thioredoxin reductase activity. L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types.
• Uses: Seleno-L-cystine can be used for the synthesis of:Biologically active selenol compounds.Non-natural selenylated diamino acids.

Technology Process of L-Selenocystine

There total 28 articles about L-Selenocystine 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: 90.0%

β-chloro-L-alanine hydrochloride (51887-89-9,3157-46-8) → seleno-L-cystine (1464-43-3,2897-21-4,26932-45-6,29621-88-3)

Guidance literature:

With selenium; sodium tetrahydroborate; at 37 ℃; pH=9;

DOI:10.1016/S0960-894X(01)00590-X

Reference yield: 84.0%

L-dibenzyl N,N'-di(benzyloxycarbonyl)selenocystinate (109276-78-0) → seleno-L-cystine (1464-43-3,2897-21-4,26932-45-6,29621-88-3)

Guidance literature:

With hydrogen bromide; In acetic acid; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88049-2

Reference yield: 82.0%

dimethyl 3,3'-diselanediyl-(2R,2'R)-bis(2-((tertbutoxycarbonyl)amino)propanoate) (195324-31-3) → seleno-L-cystine (1464-43-3,2897-21-4,26932-45-6,29621-88-3)

Guidance literature:

dimethyl 3,3'-diselanediyl-(2R,2'R)-bis(2-((tertbutoxycarbonyl)amino)propanoate); With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

With hydrogenchloride; at 75 ℃; for 12h; Further stages.;

DOI:10.1021/ol015712o

upstream raw materials:

(2R)-serine O-sulfate

O-acetyl-D-serine

Se-benzyl-L-selenocysteine

L-dibenzyl N,N'-di(benzyloxycarbonyl)selenocystinate

Downstream raw materials:

2-amino-3-benzylselanyl-propionic acid

L-selenocysteine

(2R,2'R)-3,3'-diselanediylbis(2-((tert-butoxycarbonyl)amino)propanoic acid)

Oxidized glutathione

Refernces

• 1、 Satheeshkumar, Kandhan,Raju, Saravanan,Singh, Harkesh B.,Butcher, Ray J.. "Reactivity of Selenocystine and Tellurocystine: Structure and Antioxidant Activity of the Derivatives". supporting information. p. 17513 - 17522. Retrieved 2018/11/23.
• 2、 -. "Diphosphoric acid compounds, and preparation method and application thereof". Paragraph 0137; 0159. . Retrieved 2016/10/31.