| Identification | Back Directory | [Name]
L-SELENOCYSTINE | [CAS]
29621-88-3 | [Synonyms]
L-SELENOCYSTINE
SELENO-L-CYSTINE
L-SELENOCYSTINE 98%
L-Selenocystine,98%
Seleno-L-cystine 95%
3’-diselenodi-l-alanin
3,3'-DISELENO-L-ALANINE
l-3,3’-diselenodialanine
L-Alanine,3,3'-diselenobis-
L-Selenocystine Monohydrate
Alanine, 3,3'-diselenodi-, L-
(R,R)-3,3'-DISELENO-BIS(2-AMINOPROPIONIC ACID)
2-Amino-3-(((R)-2-amino-2-carboxyethyl)diselanyl)propanoic acid
(R,R)-3,3μ-Diseleno-bis(2-aminopropionic acid), L-Selenocystine
Seleno-L-cystine,(R,R)-3,3′-Diseleno-bis(2-aminopropionic acid), L-Selenocystine | [EINECS(EC#)]
275-728-7 | [Molecular Formula]
C6H12N2O4Se2 | [MDL Number]
MFCD00800971 | [MOL File]
29621-88-3.mol | [Molecular Weight]
334.09 |
| Chemical Properties | Back Directory | [Appearance]
yellow fine powder | [Melting point ]
224.5-229.5 °C(lit.)
| [Boiling point ]
538.3±60.0 °C(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Aqueous Acid (Slightly), Aqueous Base (Slightly) | [form ]
Powder | [pka]
1.69±0.10(Predicted) | [color ]
Yellow | [Optical Rotation]
[α]20/D 28°, c = 1 in NaOH | [BRN ]
1969559 | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Chemical Properties]
yellow fine powder | [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.1,2 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.2,3 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.2,4 | [Uses]
Seleno-L-cystine can be used for the synthesis of:
- Biologically active selenol compounds.
- Non-natural selenylated diamino acids.
| [reaction suitability]
reaction type: solution phase peptide synthesis | [References]
[1] SPALLHOLZ J E. On the nature of selenium toxicity and carcinostatic activity[J]. Free Radical Biology and Medicine, 1994, 17 1: Pages 45-64. DOI: 10.1016/0891-5849(94)90007-8
[2] SOUGAT MISRA. Redox-active selenium compounds–from toxicity and cell death to cancer treatment.[J]. Nutrients, 2015, 7 5: 3536-3556. DOI: 10.3390/nu7053536
[3] BRIAN CUNNIFF . A direct and continuous assay for the determination of thioredoxin reductase activity in cell lysates[J]. Analytical biochemistry, 2013, 443 1: Pages 34-40. DOI: 10.1016/j.ab.2013.08.013
[4] MARITA WALLENBERG. Selenium induces a multi-targeted cell death process in addition to ROS formation[J]. JOURNAL OF CELLULAR AND MOLECULAR MEDICINE, 2014, 18 4: 671-684. DOI: 10.1111/jcmm.12214 |
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