81739-40-4

Basic information

• Product Name: S-Nitroso-N-acetyl-DL-penicillamine
• Synonyms: Dl-valine, N-acetyl-3-(nitrosothio)-;N-Acetyl-S-nitroso-DL-penicillamine;Snap (amino acid)
• CAS NO: 81739-40-4
• Molecular Formula: C7H12N2O4S
• Molecular Weight: 0
• Mol File: 81739-40-4.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Density: 1.36g/cm³
• Refractive Index: 1.56
• CAS DataBase Reference: S-Nitroso-N-acetyl-DL-penicillamine(CAS DataBase Reference)
• NIST Chemistry Reference: S-Nitroso-N-acetyl-DL-penicillamine(81739-40-4)
• EPA Substance Registry System: S-Nitroso-N-acetyl-DL-penicillamine(81739-40-4)

Safety Data

• Hazardous Substances Data: 81739-40-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)/t5-/m1/s1

Upstream product

• 15537-71-0 N-acetyl-3,3-dimethyl-D-cysteine 
• 67776-06-1 S-nitroso-N-acetyl-DL-penicillamine 
• 2510-38-5 N-acetyl-L-penicillamine 
• 359699-80-2 C₁₇H₂₃N₃O₃S₂ 
• 59-53-0 NAP 
• 134469-02-6 S-nitroso-L-cysteine 
• 166667-89-6 (S)-nitroso-L-cysteine ethyl ester 
• 57564-91-7 S-Nitrosoglutathione 
• 67616-46-0 S-nitroso-3-mercaptopropionic acid 
• 67616-42-6 S-nitroso-2-aminoethanethiol 
• 79032-48-7 S-nitroso-N-acetylpenicillamine 
• 52-66-4 DL-Penicillamin 
• 67616-44-8 2-hydroxy-S-nitrosoethanethiol 
• 70015-86-0 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N-oxide 

Downstream Products

• 67809-84-1 N-acetyl-D,L-penicillamine disulfide 
• 79032-48-7 S-nitroso-N-acetylpenicillamine 
• 70527-85-4 2-Acetylamino-3-methyl-3-(toluene-4-sulfonylsulfanyl)-butyric acid 

Relevant articles and documents

Versatile new reagent for nitrosation under mild conditions

Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.

Nitric oxide-releasing packaging membranes

Biodegradable composite membranes with antimicrobial properties consisting of nanocellulose fibrils, chitosan, and S-Nitroso-N-acetylpenicillamine (SNAP) were developed and tested for food packaging applications. Nitric oxide donor, SNAP was encapsulated into completely dispersed chitosan in 100 mL, 0.1N acetic acid and was thoroughly mixed with nanocellulose fibrils (CNF) to produce a composite membrane. The fabricated membranes had a uniform dispersion of chitosan and SNAP within the nanocellulose fibrils, which was confirmed through Scanning Electron Microscopy (SEM) micrographs and chemiluminescence nitric oxide analyzer. The membranes prepared without SNAP showed lower water vapor permeability than that of the membranes with SNAP. The addition of SNAP resulted in a decrease in the Young's modulus for both 2-layer and 3-layer membrane configurations. Antimicrobial property evaluation of SNAP incorporated membranes showed an effective zone of inhibition against bacterial strains of Enterococcus faecalis, Staphylococcus aureus, and Listeria monocytogenes and demonstrated its potential applications for food packaging.

Reduction in thrombosis and bacterial adhesion with 7 day implantation of S-nitroso-N-acetylpenicillamine (SNAP)-doped Elast-eon E2As catheters in sheep

Thrombosis and infection are two common problems associated with blood-contacting medical devices such as catheters. Nitric oxide (NO) is known to be a potent antimicrobial agent as well as an inhibitor of platelet activation and adhesion. Healthy endothelial cells that line the inner walls of all blood vessels exhibit a NO flux of 0.5-4 × 10-10 mol cm-2 min-1 that helps prevent thrombosis. Materials with a NO flux that is equivalent to this level are expected to exhibit similar anti-thrombotic properties. In this study, NO-releasing catheters were fabricated by incorporating S-nitroso-N-acetylpenicillamine (SNAP) in the Elast-eon E2As polymer. The SNAP/E2As catheters release physiological levels of NO for up to 20 days, as measured by chemiluminescence. Furthermore, SNAP is stable in the E2As polymer, retaining 89% of the initial SNAP after ethylene oxide (EO) sterilization. The SNAP/E2As and E2As control catheters were implanted in sheep veins for 7 days to examine the effect on thrombosis and bacterial adhesion. The SNAP/E2As catheters reduced the thrombus area when compared to the control (1.56 ± 0.76 and 5.06 ± 1.44 cm2, respectively). A 90% reduction in bacterial adhesion was also observed for the SNAP/E2As catheters as compared to the controls. The results suggest that the SNAP/E2As polymer has the potential to improve the hemocompatibility and bactericidal activity of intravascular catheters, as well as other blood-contacting medical devices (e.g., vascular grafts, extracorporeal circuits). This journal is