Chemistry:S-Nitroso-N-acetylpenicillamine

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S-Nitroso-N-acetylpenicillamine
Skeletal formula of SNAP
Ball-and-stick model of SNAP
Names
IUPAC name
S-Nitroso-N-acetylpenicillamine
Other names
N-Acetyl-3-(nitrosothio)-DL-valine
S-Nitroso-N-acetylpenicillamine
Identifiers
3D model (JSmol)
Abbreviations SNAP
ChEBI
ChEMBL
ChemSpider
UNII
Properties
C7H12N2O4S
Molar mass 220.25 g/mol
Appearance green solid
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P305+351+338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

S-Nitroso-N-acetylpenicillamine (SNAP) is the organosulfur compound with the formula ONSC(CH3)2CH(NHAc)CO2H. It is a green solid.[2]

SNAP is an S-nitrosothiol and is used as a model for the general class of S-nitrosothiols which have received much attention in biochemistry because nitric oxide and some organic nitroso derivatives serve as signaling molecules in living systems, especially related to vasodilation.[3] SNAP is derived from the amino acid penicillamine. S-Nitrosoglutathione is a related agent.

References

  1. "N3398 h S-Nitroso-N-acetyl-DL-penicillamine". Sigma-Aldric. https://www.sigmaaldrich.com/AU/en/product/sigma/n3398. 
  2. Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between Conformational Dynamics and the Redox Chemistry of S-Nitrosothiols". Journal of the American Chemical Society 121 (30): 7115–7123. doi:10.1021/ja9901314. 
  3. Zhang Y.; Hogg, N. (2005). "S-Nitrosothiols: Cellular Formation and Transport". Free Radical Biology and Medicine 38 (7): 831–838. doi:10.1016/j.freeradbiomed.2004.12.016. PMID 15749378.