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30095

Sigma-Aldrich

D-Cysteine

≥99% (RT), for peptide synthesis

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C3H7NO2S
CAS Number:
921-01-7
Molecular Weight:
121.16
Beilstein:
1721407
MDL number:
MFCD00066461
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57648407
NACRES:
NA.22

product name

D-Cysteine, ≥99% (RT)

Assay

≥99% (RT)

form

powder or crystals

optical activity

[α]20/D −7.6±1.0°, c = 5% in 5 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

~230 °C (dec.)

application(s)

peptide synthesis

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-/m1/s1

InChI key

XUJNEKJLAYXESH-UWTATZPHSA-N

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Application

D-Cysteine has been used in the functionalization of QDs for applications in photocatalysis.
It can also be used in the synthesis of:
  • cysteine-based chiral carbon dots (CDs)
  • D-luciferin and aminoluciferin analogs

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Unnatural isomer of cysteine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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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Yusuke Shibui et al.
Journal of toxicologic pathology, 30(3), 217-229 (2017-08-12)
Two 4-week repeated-dose toxicity studies were conducted to evaluate the potential toxicity of l-cysteine and d-cysteine. In one study, three groups of 6 male rats were each administered l-cysteine once daily by gavage at doses of 500, 1,000, or 2,000
J Diana Zhang et al.
Analytica chimica acta, 1036, 172-178 (2018-09-27)
The chiral analysis of enantiomers is important because bioactivity can depend strongly on stereochemistry as ligand-protein binding motifs are typically chiral. Ion mobility mass spectrometry-based methods are emerging for the rapid and sensitive chiral analysis of molecules. However, such methods
Hui Huang et al.
Mikrochimica acta, 186(5), 298-298 (2019-04-27)
The authors describe the preparation of a chiral graphene oxides (GOs) by covalent attachment of D- or L-cysteine using a one-step hydrothermal method. The resulting chiral functionalized GOs shows circular dichroism with intensities similar to those produced by the cysteines.
Matthias Jakob et al.
Physical chemistry chemical physics : PCCP, 20(31), 20347-20351 (2018-07-05)
Water-soluble ligand protected optically active silver nanostructures were synthesised in a one-step reduction and capping process mediated by thiol-containing biomolecules. The synthesis was performed successfully with d- and l-cysteine and l-glutathione. The chiroptical properties of the obtained nanostructures were investigated
Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo.
Adams ST & Miller SC
Current Opinion in Chemical Biology, 21(0), 112-120 (2004)
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