N-Acetyl-3-mercapto-D-valine

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N-Acetyl-3-mercapto-D-valine Basic information
Product Name:N-Acetyl-3-mercapto-D-valine
Synonyms:N-acetyl-3-dimethyl-DL-cysteine;N-Acetyl-D-penicillaminebiochemika;(S)-2-(Acetylamino)-3-mercapto-3-methylbutanoic acid;N-Acetyl-D-penicillaMine/N-Acetyl-3-Mercapto-D-Valine;N-Acetyl-D-penicillaMine for HPLC derivatization;(S)-2-Acetamido-3-mercapto-3-methylbutanoic acid;-2-Acetamido-3-mercapto-3-methylbutanoic acid;(2S)-2-acetamido-3-methyl-3-sulfanyl-butanoic acid
CAS:15537-71-0
MF:C7H13NO3S
MW:191.25
EINECS:239-585-4
Product Categories:Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:15537-71-0.mol
N-Acetyl-3-mercapto-D-valine Structure
N-Acetyl-3-mercapto-D-valine Chemical Properties
Melting point 185-190 °C (dec.)
Boiling point 392.7±37.0 °C(Predicted)
density 1.201±0.06 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
solubility Ethanol (Slightly), Methanol (Slightly), Trifluoroacetic Acid (Slightly)
form Solid
pka3.39±0.10(Predicted)
color White to Off-White
Optical Rotation[α]20/D +10±2°, c = 1% in ethanol
Merck 13,100
BRN 1724742
Major Applicationpeptide synthesis
InChI1S/C7H13NO3S/c1-4(9)8-5(6(10)11)7(2,3)12/h5,12H,1-3H3,(H,8,9)(H,10,11)/t5-/m0/s1
InChIKeyMNNBCKASUFBXCO-YFKPBYRVSA-N
SMILESCC(=O)N[C@@H](C(O)=O)C(C)(C)S || CC(=O)N[C@@H](C(O)=O)C(C)(C)S
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
10-23
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
N-Acetyl-3-mercapto-D-valine Usage And Synthesis
UsesProtected Penicillamin.
DefinitionChEBI: An N-acetyl-D-amino acid where the amino acid is D-penicillamine
Biological ActivityN-Acetyl-D-penicillamine (NAP or NAPA), a thiol compound, is often used as a control molecule in studies involving nitric oxide donor molecules such as S-nitroso-N-acetyl-dl-penicillamine (SNAP) and sodium nitroprusside (SNP). N-acetyl-D-penicillamine (NAPA) is also used as a heavy metal chelator.
Purification MethodsBoth forms are recrystallised from hot H2O. A pure sample of the D-form is obtained after five recrystallisations. [Crooks in The Chemistry of Penicillin Clarke, Johnson and Robinson eds, Princeton University Press, 470 1949, Review: Chain et al. Antibiotics (Oxford University Press) 2 1949, Beilstein 4 III 1662.]
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