Chemical synthesis of 5'-β-glycoconjugates of vitamin B6

Abstract

Various 5'-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to Koenigs-Knorr conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5'-β-[¹³C₆]-labeled pyridoxine glucoside (PNG) was prepared starting from [¹³C₆]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5'-β-pyridoxal glucoside (PLG).

Keywords: Chemical synthesis; Glycoconjugates; Glycosylation; Labeled; PLG; PNG; Pyridoxal; Pyridoxine; Vitamin B(6).