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545996

Sigma-Aldrich

Seleno-L-cystine

95%

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

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.
  • Non-natural selenylated diamino acids.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Poisonous substance

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

545996-250MG:4.54817316863E12
545996-1G:4.548173168623E12

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
Tianfeng Chen et al.
The international journal of biochemistry & cell biology, 41(3), 666-676 (2008-08-23)
The role of selenium as potential cancer chemopreventive and chemotherapeutic agents has been supported by epidemiological, preclinical and clinical studies. Although cell apoptosis has been evidenced as a critical mechanism mediating the anticancer activity of selenium, the underlying molecular mechanisms
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