30095

Sigma-Aldrich

D-Cysteine

≥99% (RT)

Synonym(s):
(S)-2-Amino-3-mercaptopropionic acid
Empirical Formula (Hill Notation):
C3H7NO2S
CAS Number:
Molecular Weight:
121.16
Beilstein/REAXYS Number:
1721407
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99% (RT)

optical activity

[α]20/D −7.6±1.0°, c = 5% in 5 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

application(s)

peptide synthesis: suitable

mp

~230 °C (dec.)

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

1 g in glass bottle
100 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Unnatural isomer of cysteine.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 30095.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Jing Wang et al.
Nanomaterials (Basel, Switzerland), 8(12) (2018-12-14)
Chiral recognition is of fundamental importance in chemistry and life sciences and the principle of chiral recognition is instructive in chiral separation and enantioselective catalysis. Non-chiral Ag nanoparticles (NPs) conjugated with chiral cysteine (Cys) molecules demonstrate strong circular dichroism (CD)...
Angéla Takács et al.
Scientific reports, 10(1), 14287-14287 (2020-09-02)
Bortezomib (BOZ) is a proteasome inhibitor chemotherapeutic agent utilized to treat multiple myeloma and recently offered to cure melanoma. Bortezomib-induced neuropathy is one of the dose-limiting side-effects, which can be treated with antioxidants (e.g. alpha-lipoic acid-ALA and Vitamin B1-vit B1)....
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...
Antonia Asimakopoulou et al.
British journal of pharmacology, 169(4), 922-932 (2013-03-16)
Hydrogen sulfide (H₂S) is a signalling molecule that belongs to the gasotransmitter family. Two major sources for endogenous enzymatic production of H₂S are cystathionine β synthase (CBS) and cystathionine γ lyase (CSE). In the present study, we examined the selectivity...

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