Oxidation of cholesterol and O-protected derivatives by the environmental pollutant NO₂

A N Zalewski; J G Nathanael; J M White; U Wille

doi:10.1039/c5cc09663d

Oxidation of cholesterol and O-protected derivatives by the environmental pollutant NO₂

Chem Commun (Camb). 2016 Mar 14;52(21):4060-3. doi: 10.1039/c5cc09663d.

Authors

A N Zalewski¹, J G Nathanael¹, J M White¹, U Wille¹

Affiliation

¹ School of Chemistry, Bio21 Institute, The University of Melbourne, Parkville, Victoria 3010, Australia. [email protected].

PMID: 26892038
DOI: 10.1039/c5cc09663d

Abstract

Exposure of O-protected and free cholesterol to NO2˙ under exclusion of water leads to nitroimine nitrates through a non-radical mechanism, which reveals the high susceptibility of the π system to oxidative damage. In the presence of moisture the reaction leads to 6-nitrocholesterols , which result from hydrolysis and oxidation of 2.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cholesterol / analogs & derivatives
Cholesterol / chemistry*
Environmental Pollutants / chemistry*
Free Radicals / chemistry*
Nitrates / chemistry*
Nitrogen Dioxide / chemistry*
Oxidants / chemistry*
Oxidation-Reduction

Substances

Environmental Pollutants
Free Radicals
Nitrates
Oxidants
6-nitrocholesterol
Cholesterol
Nitrogen Dioxide