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Merck

30200

Sigma-Aldrich

L-Cystin

≥99.7% (TLC)

Synonym(e):

(R,R)-3,3′-Dithio-bis-(2-aminopropionsäure)

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25 G
€ 44,00
100 G
€ 131,00
500 G
€ 427,00

About This Item

Lineare Formel:
[-SCH2CH(NH2)CO2H]2
CAS-Nummer:
Molekulargewicht:
240.30
Beilstein:
1728094
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352209
eCl@ss:
32160406
PubChem Substanz-ID:
NACRES:
NA.26

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Produktbezeichnung

L-Cystin, ≥99.7% (TLC)

Qualitätsniveau

Assay

≥99.7% (TLC)

Form

powder or crystals

Optische Aktivität

[α]20/D −219±5°, c = 1% in 1 M HCl

Glührückstand

≤0.1% (as SO4)

Verlust

≤0.1% loss on drying

Farbe

white

mp (Schmelzpunkt)

>240 °C (dec.) (lit.)

Löslichkeit

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

Anionenspuren

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

Kationenspuren

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

Anwendung(en)

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

InChIKey

LEVWYRKDKASIDU-IMJSIDKUSA-N

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Anwendung

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.[1]

Biochem./physiol. Wirkung

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.[2] Inhibition of cysteine uptake induces toxicity in neuronal cells.[3]

Sonstige Hinweise

Preparation of N,N′-dibenzoyl-L-cystine, an efficient auxiliary for enantioselective reductions of ketones[4][5]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Cystin United States Pharmacopeia (USP) Reference Standard

USP

1161586

Cystin

L-Cystin suitable for biopharmaceutical production FCC

SAFC

1.02836

L-Cystin

L-Cystin

SAFC

C5735

L-Cystin

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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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