We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine.
- Authors
Esmurziev, Aslan M.; Reimers, Arne; Andreassen, Trygve; Simic, Nebojsa; Sundby, Eirik; Hoff, Bård Helge
- 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.
- Subjects
LAMOTRIGINE; ANTICONVULSANTS; TRIAZINES; NITROMETHANE; NITROPROPANE
- Publication
Molecules, 2012, Vol 17, Issue 1, p820
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules17010820