benzoylated uronic acid building blocks and synthesis of n-uronate conjugates of lamotrigine
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2012
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Abstract
A 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.
| Reference Key |
hoff2012moleculesbenzoylated
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|---|---|
| Authors | ;Bård Helge Hoff;Eirik Sundby;Trygve Andreassen;Nebojsa Simic;Arne Reimers;Aslan M. Esmurziev |
| Journal | Journal of ethnopharmacology |
| Year | 2012 |
| DOI |
10.3390/molecules17010820
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