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P1101

Sigma-Aldrich

D-Penicillamine disulfide

97%, cell analysis

Synonym(s):

3,3′-Dithiobis(2-amino-3-methylbutanoic acid), 3,3′-Dithiobis(2-amino-3-methylbutyric acid), 3,3′-Dithiobis-D-valine, S,S′-Bi(D-penicillamine), NSC 87505

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About This Item

Linear Formula:
[-SC(CH3)2CH(NH2)CO2H]2
CAS Number:
20902-45-8
Molecular Weight:
296.41
Beilstein:
4461521
EC Number:
244-107-2
MDL number:
MFCD00004264
UNSPSC Code:
12352116
PubChem Substance ID:
24898153
NACRES:
NA.22

Product Name

D-Penicillamine disulfide, 97%

Assay

97%

form

powder or crystals

optical activity

[α]25/D −75°, c = 1 in 1 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

color

white

mp

204 °C (dec.) (lit.)

application(s)

cell analysis

SMILES string

CC(C)(SSC(C)(C)[C@@H](N)C(O)=O)[C@@H](N)C(O)=O

InChI

1S/C10H20N2O4S2/c1-9(2,5(11)7(13)14)17-18-10(3,4)6(12)8(15)16/h5-6H,11-12H2,1-4H3,(H,13,14)(H,15,16)/t5-,6-/m0/s1

InChI key

POYPKGFSZHXASD-WDSKDSINSA-N

Application

Used in pharmacological studies of:
  • Molecules dermatomyositis activity
  • Antimelanoma activity of apoptogenic carbonyl scavengers

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR7985
MKCM2360
MKCF5319
MKCD9832
MKBW8423V

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[Determination of D-penicillamine and its metabolites in blood and urine].
K Kyogoku et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 102(4), 322-327 (1982-04-01)
Anshul Gupte et al.
Journal of inorganic biochemistry, 101(4), 594-602 (2007-02-06)
D-Penicillamine is a potent copper (Cu) chelating agent. D-Pen reduces Cu(II) to Cu(I) in the process of chelation while at the same time being oxidized to D-penicillamine disulfide. It has been proposed that hydrogen peroxide is generated during this process.
Amit K Galande et al.
Biopolymers, 71(5), 534-551 (2003-11-25)
A recently rediscovered reaction of base-assisted lanthionine formation has been applied to several systems of disulfide-bridged peptides. In addition to previously described nonapeptides consisting of i, i+3 cystine linkages, the reaction has now been extended to systems consisting of shorter
M J Willemsen et al.
International journal of dermatology, 29(3), 193-197 (1990-04-01)
Pemphigus erythematosus occurred in a patient with rheumatoid arthritis who was treated with D-penicillamine. The skin lesions appeared 4 months after the onset of D-penicillamine treatment and persisted 14 years after cessation of this drug. Topical betamethasone dipropionate applications resulted
J C Crawhall
Clinical and investigative medicine. Medecine clinique et experimentale, 7(1), 31-34 (1984-01-01)
Penicillamine disulfides have been analysed by automatic amino acid analysis. Because the free thiol reacts poorly with ninhydrin, other detection methods are preferred, particularly high pressure liquid chromatography using an electrochemical detector or gas chromatography with a flame ionization detector.
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