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Benzoylated uronic Acid building blocks and synthesis of N-uronate conjugates of lamotrigine

Esmurziev, Aslan; Reimers, Arne; Andreassen, Trygve; Simic, Nebojsa; Sundby, Eirik; Hoff, Bård Helge
Journal article, Peer reviewed
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URI
http://hdl.handle.net/11250/2359503
Date
2012
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Original version
Molecules 2012, 17(1):820-835   10.3390/molecules17010820
Abstract
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.
Publisher
MDPI
Journal
Molecules

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