S-Nitrosothiol

Structure of an S–nitrosothiol. R denotes some organic group.

In organic chemistry, S-nitrosothiols, also known as thionitrites, are organic compounds or functional groups containing a nitroso group attached to the sulfur atom of a thiol.[1] S-Nitrosothiols have the general formula R−S−N=O, where R denotes an organic group.

S-Nitrosothiols have received much attention in biochemistry because they serve as donors of both the nitrosonium ion NO+ and of nitric oxide and thus best rationalize the chemistry of NO-based signaling in living systems, especially related to vasodilation.[2] Red blood cells, for instance, carry an essential reservoir of S-nitrosohemoglobin and release S-nitrosothiols into the bloodstream under low-oxygen conditions, causing the blood vessels to dilate.[3]

  1. ^ "Nitroso" IUPAC nomenclature
  2. ^ 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.
  3. ^ Diesen, Diana L.; Douglas T. Hess; Jonathan S. Stamler (2008). "Hypoxic vasodilation by red blood cells: evidence for an S-nitrosothiol-based signal". Circulation Research. 103 (5): 545–53. doi:10.1161/CIRCRESAHA.108.176867. PMC 2763414. PMID 18658051.