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545996

Sigma-Aldrich

Seleno-L-cystine

95%, for peptide synthesis

Synonym(s):

(R,R)-3,3′-Diseleno-bis(2-aminopropionic acid), L-Selenocystine

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About This Item

Linear Formula:
CO2HCH(NH2)CH2(Se)2CH2CH(NH2)CO2H
CAS Number:
29621-88-3
Molecular Weight:
334.09
Beilstein/REAXYS Number:
1969559
MDL number:
MFCD00800971
UNSPSC Code:
12352209
PubChem Substance ID:
24878867
NACRES:
NA.22

product name

Seleno-L-cystine, 95%

assay

95%

form

powder or crystals

optical activity

[α]20/D −28°, c = 1 in NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

224.5-229.5 °C (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

N[C@@H](C[Se][Se]C[C@H](N)C(O)=O)C(O)=O

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

InChI key

JULROCUWKLNBSN-IMJSIDKUSA-N

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Application

Seleno-L-cystine can be used for the synthesis of:
  • Biologically active selenol compounds.
  • Non-natural selenylated diamino acids.

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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Andrzej Gawor et al.
Animals : an open access journal from MDPI, 10(5) (2020-05-13)
Identification and quantification of the selenium species in biological tissues is imperative, considering the need to properly understand its metabolism and its importance in various field of sciences, especially nutrition science. Although a number of studies deals with the speciation
Novel selenium-containing non-natural diamino acids
Caputo R, et al.
Tetrahedron Letters, 48(8), 1425-1427 (2007)
Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: evaluation of kinetics of ?-elimination reactions in rat renal cytosol
Andreadou I, et al.
Journal of Medicinal Chemistry, 39(10), 2040-2046 (1996)
Amit Kunwar et al.
Radiation and environmental biophysics, 50(2), 271-280 (2011-01-25)
Selenocystine (CysSeSeCys), a diselenide aminoacid exhibiting glutathione peroxidase-like activity and selective antitumor effects, was examined for in vivo antigenotoxic and antioxidant activity in Swiss albino mice after exposure to a sublethal dose (5 Gy) of γ-radiation. For this, CysSeSeCys was administered
Eric Olm et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(27), 11400-11405 (2009-06-25)
The selenium salt selenite (SeO(3)(2-)) is cytotoxic in low to moderate concentrations, with a remarkable specificity for cancer cells resistant to conventional chemotherapy. Our data show that selenium uptake and accumulation, rather than intracellular events, are crucial to the specific
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