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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:
1969559
MDL number:
MFCD00800971
UNSPSC Code:
12352209
PubChem Substance ID:
24878867
NACRES:
NA.22
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Product Name

Seleno-L-cystine, 95%

Quality Level

100

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.[1]
  • Non-natural selenylated diamino acids.[2]

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7076
MKCS0705
MKCR0273
MKCM2257
MKCG7616

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I Andreadou et al.
Journal of medicinal chemistry, 39(10), 2040-2046 (1996-05-10)
Eighteen Se-substituted selenocysteine derivatives were synthesized as potential kidney selective prodrugs which can be activated by renal cysteine conjugate beta-lyase to selenium-containing chemoprotectants or antitumor agents. Selenocysteine derivatives with aliphatic and benzylic Se-substituents were synthesized by reducing selenocystine to selenocysteine
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)
Novel selenium-containing non-natural diamino acids
Caputo R, et al.
Tetrahedron Letters, 48(8), 1425-1427 (2007)
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
Erin E Battin et al.
Metallomics : integrated biometal science, 3(5), 503-512 (2011-02-03)
Copper and iron are two widely studied transition metals associated with hydroxyl radical (˙OH) generation, oxidative damage, and disease development. Because antioxidants ameliorate metal-mediated DNA damage, DNA gel electrophoresis assays were used to quantify the ability of ten selenium-containing compounds
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