Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate

Aneta M Tomkiel; Leszek Siergiejczyk; Dorota Naróg; Jolanta Płoszyńska; Andrzej Sobkowiak; Jacek W Morzycki

doi:10.1016/j.steroids.2016.05.011

Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate

Steroids. 2017 Jan:117:44-51. doi: 10.1016/j.steroids.2016.05.011. Epub 2016 Jun 2.

Authors

Aneta M Tomkiel¹, Leszek Siergiejczyk¹, Dorota Naróg², Jolanta Płoszyńska², Andrzej Sobkowiak², Jacek W Morzycki³

Affiliations

¹ Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland.
² Faculty of Chemistry, Rzeszów University of Technology, P. O. Box 85, 35-959 Rzeszów, Poland.
³ Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245 Białystok, Poland. Electronic address: morzycki@uwb.edu.pl.

PMID: 27263439
DOI: 10.1016/j.steroids.2016.05.011

Abstract

Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective - primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.

Keywords: Cholesterol; Cholesteryl diphenylphosphate; Cholesterylation; Electrochemical oxidation; Glycosylation.

Publication types

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

MeSH terms

Cholesterol / chemistry*
Cholesterol / metabolism*
Electrochemistry / methods*
Glycosylation
Molecular Structure
Stereoisomerism

Substances

Cholesterol