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C7602

Sigma-Aldrich

L-Cystine

from non-animal source, meets EP testing specifications, suitable for cell culture, 98.5-101.0%

Synonym(s):

(R,R)-3,3′-Dithiobis(2-aminopropionicacid)

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About This Item

Linear Formula:
[-SCH2CH(NH2)CO2H]2
CAS Number:
56-89-3
Molecular Weight:
240.30
Beilstein/REAXYS Number:
1728094
EC Number:
200-296-3
MDL number:
MFCD00064228
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24892973
NACRES:
NA.26

biological source

non-animal source

Quality Level

200

agency

meets EP testing specifications

product line

BioXtra

assay

98.5-101.0%

form

powder

technique(s)

cell culture | mammalian: suitable

impurities

endotoxin, tested

color

white to off-white

mp

>240 °C (dec.) (lit.)

solubility

1 M HCl: 100 mg/mL

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C6H12N2O4S2/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

LEVWYRKDKASIDU-IMJSIDKUSA-N

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Application

L-Cystine has been used as a supplement in astroglial-conditioned media to culture cerebral astroglia. It has been used in several techniques, such as HPLC-FD, UHPLC-UV, UHPLC-MS, and triple quadrupole tandem mass spectrometry (UHPLC-MS/MS), to differentiate BMAA (β-N-methylamino-L-alanine), the cyanobacterial neurotoxin, from other diamino acids.
L-Cystine has been used as a supplement in oocyte culture media to improve oocyte maturation and parthenogenesis of embryonic development.

Biochem/physiol Actions

Cystinuria is characterized with renal transport and excretion of L-Cystine. Cysteine is one of the functional amino acids that are associated with growth, reproduction, maintenance and immunity. Cysteine is a source of disulfide linkage in protein and is associated with sulfur transport. At physiological pH, cysteine undergoes rapid oxidation to form cystine. Reduced availability of cysteine or cystine, influences leukocyte metabolism. L-Cystine is necessary for oxygen production and LDL (low density lipoprotein) modification by arterial smooth muscle cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Studies on Analogues of L-Cysteine and L-Cystine
Austin S and Leif G
Blood (2018)
Mutation of Ataxia?Telangiectasia Mutated is Associated with Dysfunctional Glutathione Homeostasis in Cerebellar Astroglia
Andrew Campbell
Glia, 64(2), 227-239 (2016)
Transport Interaction of t-Cystine and L-Glutamate in Human Diploid
Fibroblasts in Culture
Shiro Bannai and Emi Kitamur
The Journal of Biological Chemistry, 255(6), 2372- 2376 (1980)
Using cysteine/cystine to overcome oxidative stress in goat oocytes and embryos cultured in vitro
Zhengrong Zhou
Molecular Medicine Reports, 14(2) (2016)
Distinguishing the cyanobacterial neurotoxin b-N-methylamino-L-alanine
(BMAA) from other diamino acids
S.A. Banack
Toxicon (2011)
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Cysteine in Cell Culture

Importance and uses of cysteine in serum-free eukaryotic, including hybridoma and Chinese Hamster Ovary (CHO) cell, cultures

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