ChemicalBook Product Catalog Chemical Reagents Organic reagents Selenium compounds L-SELENOCYSTINE

L-SELENOCYSTINE

Product NameL-SELENOCYSTINE
CAS29621-88-3
MFC6H12N2O4Se2
MW334.09
EINECS608-382-6
MOL File29621-88-3.mol

Chemical Properties

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)
pka	1.69±0.10(Predicted)
form	Powder
color	Yellow
optical activity	[α]20/D 28°, c = 1 in NaOH
BRN	1969559
Stability	Hygroscopic
Major Application	peptide synthesis
InChI	1S/C6H12N2O4Se2/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-/m0/s1
InChIKey	JULROCUWKLNBSN-IMJSIDKUSA-N
SMILES	N[C@@H](C[Se][Se]C[C@H](N)C(O)=O)C(O)=O

Safety Information

Hazard Codes	T,N
Risk Statements	23/25-33-50/53
Safety Statements	20/21-28-45-60-61
RIDADR	UN 3283 6.1/PG 3
WGK Germany	3
RTECS	AY6032000
HazardClass	6.1
PackingGroup	III
HS Code	29319090
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 STOT RE 2

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

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 K_m = 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.

Chemical Properties

yellow fine powder

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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