Skip to Content
Merck
All Photos(1)

Key Documents

779539

Sigma-Aldrich

L-Cystine

produced by Wacker Chemie AG, Burghausen, Germany, ≥98.5%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
[-SCH2CH(NH2)CO2H]2
CAS Number:
Molecular Weight:
240.30
Beilstein:
1728094
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

Quality Level

Assay

≥98.5%

form

powder

optical activity

[α]/D -224 to -218°

reaction suitability

reaction type: solution phase peptide synthesis

impurities

≤0.02% ammonium
≤0.2% ninhidrin positive substances (each)
≤10 ppm heavy metals

ign. residue

≤0.1%

loss

≤0.2% loss on drying

mp

>240 °C (dec.) (lit.)

anion traces

chloride (Cl-): ≤200 ppm
sulfate (SO42-): ≤300 ppm

cation traces

As: ≤1 ppm
Fe: ≤10 ppm
Pb: ≤5 ppm

suitability

clear, colorless for appearance of solution

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

Looking for similar products? Visit Product Comparison Guide

General description

L-Cystine is an amino acid mainly found in the keratin of hair.
This product is supplied from Wacker FERMOPURE® material, but is sold for R&D use only, not for drug, household or other uses.

Application

L-Cystine can be used as a starting material for the synthesis of d-biotin, aromatic-bridged cystine cyclic peptides (cystinophanes), chiral imidazolidine disulfides and biodegradable PEGylated gadolinium-diethylenetriamine pentaacetic acid (Gd-DTPA) L-cystine copolymers.

Legal Information

FERMOPURE is a registered trademark of Wacker Chemie AG

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of d-biotin from L-cystine via intramolecular [3+ 2] cycloaddition
Baggiolini E G, et al.
Journal of the American Chemical Society, 104(23), 6460-6462 (1982)
Synthesis of new chiral imidazolidine disulfides derived from l-cystine and their application in the enantioselective addition of diethylzinc to aldehydes
Braga A L, et al.
Tetrahedron Letters, 43(13), 2335-2337 (2002)
PEG-g-poly (GdDTPA-co-L-cystine): a biodegradable macromolecular blood pool contrast agent for MR imaging.
Mohs A M, et al.
Bioconjugate Chemistry, 15(6), 1424-1430 (2004)
L-Cystine
Gortner RA and Hoffman WF
Organic Syntheses, 5, 39-39 (1925)
Cystinophanes, a novel family of aromatic-bridged cystine cyclic peptides: synthesis, crystal structure, molecular recognition, and conformational studies.
Ranganathan D, et al.
Journal of the American Chemical Society, 120(12), 2695-2702 (1998)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service