Chemical synthesis of 5'-β-glycoconjugates of vitamin B.

Carbohydr Res

Chair of Analytical Food Chemistry, Technical University of Munich, Maximus-von-Imhof-Forum 2, 85354, Freising, Germany. Electronic address:

Published: March 2020

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-[C]-labeled pyridoxine glucoside (PNG) was prepared starting from [C]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5'-β-pyridoxal glucoside (PLG).

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http://dx.doi.org/10.1016/j.carres.2020.107940DOI Listing

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