D-Penicillamine, a reducing and chelating agent, is used in the treatment of rheumatoid arthritis. It is less toxic than the L-enantiomer. Due to its ability to chelate copper and zinc ions, which are involved in Aβ 1-42 accumulation in the brain, D-penicillamine bound to carriers may find use in the therapy of Alzheimer’s disease.
The amino acid is a characteristic degradation product of penicillin-type antibiotics.
F-4235
H-D-Pen-OH
Synonym:
H-β,β-Dimethyl-D-Cys-OH, H-β-Mercapto-D-Val-OH
| C5H11NO2S | Mr: 149.21 | [52-67-5] |
| Longterm storage temperature: | RT | C5H11NO2S |
Literature:
R.C.Siegel, J. Biol. Chem., 252, 254 (1977)
G.Starkebaum and R.K.Root, J. Immunol., 134, 3371 (1985)
T.A.Medsger Jr. et al., Scand. J. Rheumatol., 30, 192 (2001)
Z.Cui et al., Eur. J. Pharm. Biopharm., 59, 263 (2005)
Merck Index, 14th ed., No. 7088, (2006)
R.C.Siegel, J. Biol. Chem., 252, 254 (1977)
G.Starkebaum and R.K.Root, J. Immunol., 134, 3371 (1985)
T.A.Medsger Jr. et al., Scand. J. Rheumatol., 30, 192 (2001)
Z.Cui et al., Eur. J. Pharm. Biopharm., 59, 263 (2005)
Merck Index, 14th ed., No. 7088, (2006)
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Family Description:
Corresponds to β,β-dimethylcysteine or β-mercaptovaline. For an S-protected derivative of deamino-penicillamine please see Q-1610.
The rigidity of disulfide bridges can be increased by replacing Cys by Pen. Pen analogs of enkephalins, RGD-peptides, urotensin and further active peptides with improved potency and/or selectivity have been described.
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