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Sigma-Aldrich

L-Cysteine

≥98.5% (RT), suitable for HPLC, BioUltra

Synonym(s):

(R)-2-Amino-3-mercaptopropionic acid

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About This Item

Linear Formula:
HSCH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
121.16
Beilstein:
1721408
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

product name

L-Cysteine, BioUltra, ≥98.5% (RT)

product line

BioUltra

Assay

≥98.5% (RT)

form

powder or crystals

optical activity

[α]20/D +8.0±0.5°, c = 5% in 5 M HCl

technique(s)

HPLC: suitable

impurities

insoluble matter, passes filter test
≤0.5% foreign amino acids

ign. residue

≤0.05% (as SO4)

loss

≤0.05% loss on drying, 20 °C (HV)

color

white

mp

240 °C (dec.) (lit.)

solubility

1 M HCl: 1 M at 20 °C, clear, colorless

anion traces

chloride (Cl-): ≤100 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Al: ≤5 mg/kg
As: ≤0.1 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
NH4+: ≤500 mg/kg
Na: ≤100 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

λ

1 M in 1 M HCl

UV absorption

λ: 260 nm Amax: 1.5
λ: 280 nm Amax: 0.2

SMILES string

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

InChI

1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

InChI key

XUJNEKJLAYXESH-REOHCLBHSA-N

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Application

L-Cysteine has been used in quenching of unreacted maleimide during antibody grafting. It has also been used in the preparation of nitrosocysteine stock solution, that has been employed to induce S-nitrosylation to achieve reversible cysteine modification.

Biochem/physiol Actions

Cysteine is one of the functional amino acids that regulates metabolism for growth, reproduction, maintenance and immunity. Cysteine provides the disulfide linkage in proteins. It is directly associated with the transport of sulfur. Taurine, a metabolic product of cysteine acts as an antioxidant and controls the cellular redox state. Cysteine is involved in the formation of hydrogen sulfide that is utilized as a signaling molecule.
NMDA glutamatergic receptor agonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Journal of Controlled Release : Official Journal of the Controlled Release Society, 156(2), 118-127 (2011)
Resin-assisted enrichment of thiols as a general strategy for proteomic profiling of cysteine-based reversible modifications
Jia Guo
Nature Protocols, 9(1), 64-75 (2014)
Amino acids: metabolism, functions, and nutrition
Guoyao Wu
Amino Acids, 37(1), 1-17 (2009)
Nicholas Kwiatkowski et al.
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Journal of agricultural and food chemistry, 62(26), 6183-6189 (2014-06-01)
The present study examined the impact of the supplementation of glutathione (GSH), γ-L-glutamyl-L-cysteinyl-glycine, on human blood GSH levels. Healthy human volunteers were orally supplemented with GSH (50 mg/kg body weight). Venous blood was collected from the cubital vein before and

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