Issue 21, 2009
From the journal:

Chemical Communications

The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterolin vivo†

Anita D. Wentworth,a   Byeong-Doo Song,a   Jorge Nieva,b   Asher Shafton,a   Sangeetha Tripurenania  and  Paul Wentworth Jr.*ac  

* Corresponding authors

a Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, USA
E-mail: paulw@scripps.edu
Fax: +1 858 784 7385
Tel: +1 858 784 2576

b Department of Molecular and Experimental Medicine, The Scripps Research Institute, John Jay Hopkins Dr., La Jolla, USA

c Department of Biochemistry, The University of Oxford, South Parks Rd., Oxford, UK

Abstract

Ongoing efforts to unravel the origins of the cholesterol 5,6-secosterols (1a and 1b) in biological systems have revealed that the two known chemical routes to these oxysterols, ozonolysis of cholesterol (3) and Hock-cleavage of 5-α-hydroperoxycholesterol (4a), are distinguishable based upon the ratio of the hydrazone derivatives (2a and 2b) formed in each case and this ratio offers an insight into the chemical origin of the secosterols in vivo.

Graphical abstract: The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterolin vivo

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Article information

DOI
https://doi.org/10.1039/B821584G
Article type
Communication
Submitted
02 Dec 2008
Accepted
11 Mar 2009
First published
16 Apr 2009

Chem. Commun., 2009, 3098-3100

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The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterolin vivo

A. D. Wentworth, B. Song, J. Nieva, A. Shafton, S. Tripurenani and P. Wentworth Jr., Chem. Commun., 2009, 3098 DOI: 10.1039/B821584G

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