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779539

Sigma-Aldrich

L-Cystine

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

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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:
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

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1 of 4

This Item
49603C760230200
vibrant-m

779539

L-Cystine

-
vibrant-m

49603

L-Cystine

-
vibrant-m

C7602

L-Cystine

Premium Grade
vibrant-m

30200

L-Cystine

-
reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

-

reaction suitability

-

reaction suitability

-

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

mp

>240 °C (dec.) (lit.)

mp

>240 °C (dec.) (lit.)

mp

>240 °C (dec.) (lit.)

mp

>240 °C (dec.) (lit.)

form

powder

form

-

form

powder

form

powder or crystals

grade

produced by Wacker Chemie AG, Burghausen, Germany

grade

certified reference material, TraceCERT®

grade

-

grade

-

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

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


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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)
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)
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)
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)
L-Cystine
Gortner RA and Hoffman WF
Organic Syntheses, 5, 39-39 (1925)

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