Electrochemical synthesis of glycoconjugates from activated sterol derivatives

Aneta M Tomkiel; Jan Kowalski; Jolanta Płoszyńska; Leszek Siergiejczyk; Zenon Lotowski; Andrzej Sobkowiak; Jacek W Morzycki

doi:10.1016/j.steroids.2014.01.007

Electrochemical synthesis of glycoconjugates from activated sterol derivatives

Steroids. 2014 Apr:82:60-7. doi: 10.1016/j.steroids.2014.01.007. Epub 2014 Jan 30.

Authors

Aneta M Tomkiel¹, Jan Kowalski², Jolanta Płoszyńska², Leszek Siergiejczyk¹, Zenon Lotowski¹, Andrzej Sobkowiak², Jacek W Morzycki³

Affiliations

¹ Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399 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, Hurtowa 1, 15-399 Białystok, Poland. Electronic address: morzycki@uwb.edu.pl.

PMID: 24486463
DOI: 10.1016/j.steroids.2014.01.007

Abstract

Several derivatives of cholesterol and other 3β-hydroxy-Δ(5)-steroids were prepared and tested as sterol donors in electrochemical reactions with sugar alcohols. The reactions afforded glycoconjugates with sugar linked to a steroid moiety by an ether bond. Readily available sterol diphenylphosphates yielding up to 54% of the desired glycoconjugate were found to be the best sterol donors.

Keywords: Activating groups; Cholesterol; Electrochemical oxidation; Glycosylation; Sterol glycoconjugates.

Publication types

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

MeSH terms

Electrochemical Techniques*
Glycoconjugates / chemical synthesis*
Glycoconjugates / chemistry
Molecular Conformation
Sterols / chemistry*

Substances

Glycoconjugates
Sterols