30200

Sigma-Aldrich

L-Cystine

≥99.7% (TLC)

Synonym(s):
(R,R)-3,3′-Dithiobis(2-aminopropionicacid)
Linear Formula:
[-SCH2CH(NH2)CO2H]2
CAS Number:
Molecular Weight:
240.30
Beilstein/REAXYS Number:
1728094
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥99.7% (TLC)

form

powder or crystals

optical activity

[α]20/D −219±5°, c = 1% in 1 M HCl

application(s)

peptide synthesis: suitable

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

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 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.

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
K. Soai et al.
Journal of the Chemical Society. Chemical Communications, 413-413 (1984)
Philip J Hogg
Nature reviews. Cancer, 13(6), 425-431 (2013-05-11)
Protein action in nature is generally controlled by the amount of protein produced and by chemical modification of the protein, and both are often perturbed in cancer. The amino acid side chains and the peptide and disulphide bonds that bind...

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