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Merck
CN

30200

L-Cystine

≥99.7% (TLC)

Synonym(s):

(R,R)-3,3′-Dithiobis(2-aminopropionic acid)

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About This Item

Linear Formula:
[-SCH2CH(NH2)CO2H]2
CAS Number:
56-89-3
Molecular Weight:
240.30
NACRES:
NA.26
PubChem Substance ID:
329753347
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
200-296-3
MDL number:
MFCD00064228
Beilstein/REAXYS Number:
1728094

Key Documents

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Product Name

L-Cystine, ≥99.7% (TLC)

InChI key

LEVWYRKDKASIDU-IMJSIDKUSA-N

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

SMILES string

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

assay

≥99.7% (TLC)

form

powder or crystals

optical activity

[α]20/D −219±5°, c = 1% in 1 M HCl

ign. residue

≤0.1% (as SO4)

loss

≤0.1% loss on drying

color

white

mp

>240 °C (dec.) (lit.)

solubility

1 M HCl: 0.5 g/10 mL, clear, colorless

anion traces

chloride (Cl-): ≤500 mg/kg
sulfate (SO42-): ≤100 mg/kg

cation traces

Ca: ≤50 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤6 mg/kg
Fe: ≤10 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤150 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

application(s)

peptide synthesis

Quality Level

200

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Biochem/physiol Actions

Cystine is required for the synthesis of glutathione that protects the cells from oxidative stress. A specific x(c)-cysteine/glutamate antiporter mediates cellular uptake of cysteine in exchange for glutamate. Inhibition of cysteine uptake induces toxicity in neuronal cells.

Other Notes

Preparation of N,N′-dibenzoyl-L-cystine, an efficient auxiliary for enantioselective reductions of ketones

Application

L-Cystine has been used to prepare stock solution which in turn is utilized for determining the L-cysteine and L-cystine in pharmaceutical preparations as well as in urine samples by using spectrofluorimetric flow injection method.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7407
BCCM2201
BCCL1340
BCCJ0389
BCCJ0388

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K. Soai et al.
Journal of the Chemical Society. Chemical Communications, 413-413 (1984)
Journal of the Chemical Society. Chemical Communications, 801-801 (1987)
T H Murphy et al.
Neuron, 2(6), 1547-1558 (1989-06-01)
Glutamate binds to both excitatory neurotransmitter binding sites and a Cl(-)-dependent, quisqualate- and cystine-inhibited transport site on brain neurons. The neuroblastoma-primary retina hybrid cells (N18-RE-105) are susceptible to glutamate-induced cytotoxicity. The Cl(-)-dependent transport site to which glutamate and quisqualate (but
T Pérez-Ruiz et al.
The Analyst, 117(6), 1025-1028 (1992-06-01)
A flow injection configuration is proposed for the determination of L-cysteine and L-cystine individually and for mixtures of both analytes. The procedure is based on the rapid oxidation of L-cysteine by thallium(III) with concomitant formation of fluorescent thallium(I). The inclusion
Ojore Benedict Valentine Oka et al.
Molecular cell, 50(6), 793-804 (2013-06-19)
ERdj5 is a member of the protein disulfide isomerase family of proteins localized to the endoplasmic reticulum (ER) of mammalian cells. To date, only a limited number of substrates for ERdj5 are known. Here we identify a number of endogenous
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