Electrochemical synthesis of glycoconjugates from activated sterol derivatives.
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.
Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399 Białystok, Poland.
Aneta M
AM
Tomkiel
Faculty of Chemistry, Rzeszów University of Technology, P.O. Box 85, 35-959 Rzeszów, Poland.
Jan
J
Kowalski
Faculty of Chemistry, Rzeszów University of Technology, P.O. Box 85, 35-959 Rzeszów, Poland.
Jolanta
J
Płoszyńska
Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399 Białystok, Poland.
Leszek
L
Siergiejczyk
Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399 Białystok, Poland.
Zenon
Z
Lotowski
Faculty of Chemistry, Rzeszów University of Technology, P.O. Box 85, 35-959 Rzeszów, Poland.
Andrzej
A
Sobkowiak
Institute of Chemistry, University of Białystok, Hurtowa 1, 15-399 Białystok, Poland. Electronic address: morzycki@uwb.edu.pl.
Jacek W
JW
Morzycki
D055664:Electrochemical Techniques; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013261:Sterols / Q000737:chemistry*
D006001:Glycoconjugates; D013261:Sterols
Activating groups; Cholesterol; Electrochemical oxidation; Glycosylation; Sterol glycoconjugates