Chemical glucosylation of pyridoxine. (March 2020)

• Record Type: Journal Article
• Authors: Bachmann, Thomas; Rychlik, Michael
• Is Part Of: Carbohydrate research. Volume 489(2020)
• Publication Date: 2020-03
• Subjects: Pyridoxine -- Vitamin B6 -- Chemical glycosylation -- Chemical synthesis; Bn Benzyl -- Bz Benzoyl -- LG Leaving group -- P Protecting group -- Piv Pivaloyl -- PN Pyridoxine -- PL Pyridoxal -- PM Pyridoxamine -- PLP Pyridoxal phosphate -- PMP Pyridoxamine phosphate -- PNG Pyridoxine glucoside; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2020.107929
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: The chemical synthesis of pyridoxine-5′- β -d -glucoside (5′- β -PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α 4, 3- O -isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2, 3, 4, 6-tetra- O -acetyl-d -glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′- β -PNG. Graphical abstract: Image 1 Highlights: New strategies for the chemical glucosylation of pyridoxine were investigated. Multiple leaving groups, protecting groups and promoters were tested. The synthesis gave best results using 2, 3, 4, 6-tetra- O -acetyl-d -glucopyranosyl fluoride. Formation of othoesters can be reduced by increased amounts of promoter.