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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)

Quality Level

100

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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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
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
Yu-Ting Tseng et al.
Analytical chemistry, 90(12), 7283-7291 (2018-05-23)
Stereospecific recognition of chiral molecules is ubiquitous in chemical and biological systems, thus leading to strong demand for the development of enantiomeric drugs, enantioselective sensors, and asymmetric catalysts. In this study, we demonstrate the ratio of d-Cys and l-Cys playing
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