N-Acetyl-D-penicillamine - ≥98% , CAS No.15537-71-0

CAS: 15537-71-0 Cat. No.: N140020 Molecular Weight: 191.25 Beilstein Registry Number: 1724742 EC Number: 239-585-4

GRADE & PURITY ≥98%

Synonyms

N-Acetyl-D-penicillamine|15537-71-0|N-Acetylpenicillamine|N-Acetyl-3-mercapto-D-valine|D-Valine, N-acetyl-3-mercapto-|(s)-2-acetamido-3-mercapto-3-methylbutanoic acid|N-Acetyl-3-mercaptovaline|(2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid|N-acetyl-3-s

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

N-Acetyl-D-penicillamine is a protected Penicillamine. It is used as a chiral reagent for the precolumn derivatization of amino acids and amino alcohols. Also, it is often used as a control in studies surrounding nitric oxide donor molecules.
Chiral reagent for the precolumn derivatization of amino acids or amino alcohols; the diastereoisomers formed can be efficiently resolved by HPLC on conventional reversed-phase columns1

Specifications

Synonyms

N-Acetyl-D-penicillamine | 15537-71-0 | N-Acetylpenicillamine | N-Acetyl-3-mercapto-D-valine | D-Valine, N-acetyl-3-mercapto- | (s)-2-acetamido-3-mercapto-3-methylbutanoic acid | N-Acetyl-3-mercaptovaline | (2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid | N-acetyl-3-s

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

N-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 (NA

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=O)NC(C(=O)O)C(C)(C)S
• IUPAC Name: (2S)-2-acetamido-3-methyl-3-sulfanylbutanoic acid
• InChIKey: MNNBCKASUFBXCO-YFKPBYRVSA-N
• INCHI: 1S/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
• Isomeric SMILES: CC(=O)N[C@@H](C(=O)O)C(C)(C)S
• WGK Germany: 3
• Molecular Weight: 191.25
• Beilstein: 1724742
• Reaxy-Rn: 1724743
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1724743&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 N-acyl-alpha amino acids and derivatives
              • Level8 N-acyl-alpha amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - N-acyl-alpha amino acids and derivatives
• Direct Parent: N-acyl-alpha amino acids
• Alternative Parents: Valine and derivatives Thia fatty acids Methyl-branched fatty acids Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidic acids Alkylthiols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acyl-alpha-amino acid - Valine or derivatives - Branched fatty acid - Thia fatty acid - Methyl-branched fatty acid - Fatty acid - Fatty acyl - Alkylthiol - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organic oxygen compound - Organooxygen compound - Organosulfur compound - Organopnictogen compound - Organic oxide - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
• External Descriptors: N-acetyl-D-amino acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: air sensitive
• Molecular Weight: 191.250 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 191.062 Da
• Monoisotopic Mass: 191.062 Da
• Topological Polar Surface Area: 67.400 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 203.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Fan Jia, Weijiang Yu, Xinfang Li, Yonghang Chen, Youxiang Wang, Jian Ji.  (2022)  Microneedles loaded with glutathione-scavenging composites for nitric oxide enhanced photodynamic therapy of melanoma.  Bioengineering & Translational Medicine,  8  (1): (e10352).  [PMID:36684091] [10.1002/btm2.10352]

2. Jie Chen, Hui Zhang, Yuxin Lin, Jinyu Liu, Yisong Chen, Xiaoyan Zhang, Hetong Lin, Da-Peng Yang.  (2025)  Chitosan-SNAP composite coating with sustained NO release for microbial killing and tomato preservation.  FOOD CHEMISTRY,      [PMID:41391408] [10.1016/j.foodchem.2025.147427]