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dc.contributor.authorEsmurziev, Aslan
dc.contributor.authorReimers, Arne
dc.contributor.authorAndreassen, Trygve
dc.contributor.authorSimic, Nebojsa
dc.contributor.authorSundby, Eirik
dc.contributor.authorHoff, Bård Helge
dc.identifier.citationMolecules 2012, 17(1):820-835nb_NO
dc.description.abstractA chemoenzymatic approach towards benzoylated uronic acid building blocks has been investigated starting with benzoylated hexapyranosides using regioselective C-6 enzymatic hydrolysis as the key step. Two of the building blocks were reacted with the antiepileptic drug lamotrigine. Glucuronidation of lamotrigine using methyl (2,3,4-tri-O-benzoyl-α-D-glycopyranosyl bromide)uronate proceeded to give the N2-conjugate. However, lamotrigine-N2-glucuronide was most efficiently synthesised from methyl (2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide)uronate. Employing nitromethane as solvent with CdCO3 as a base lamotrigine-N2 glucuronide was prepared in a high yield (41%). Also methyl (2,3-di-O-benzoyl-4-deoxy-4-fluoro-α-D-glucosyl bromide)uronate underwent N-glucuronidation, but the product was unstable, eliminating hydrogen fluoride to give the corresponding enoate conjugate.nb_NO
dc.rightsNavngivelse 3.0 Norge*
dc.titleBenzoylated uronic acid building blocks and synthesis of N-uronate conjugates of lamotriginenb_NO
dc.typeJournal articlenb_NO
dc.typePeer reviewednb_NO

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