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Molecules 2012, 17(1), 820-835; doi:10.3390/molecules17010820
Article

Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine

1,2, 3, 4, 1, 2,*  and 1
Received: 7 December 2011 / Revised: 2 January 2012 / Accepted: 4 January 2012 / Published: 16 January 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.
Keywords: uronic acid building blocks; lamotrigine-N2-glucuronide; fluorinated carbohydrates uronic acid building blocks; lamotrigine-N2-glucuronide; fluorinated carbohydrates
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Esmurziev, A.M.; Reimers, A.; Andreassen, T.; Simic, N.; Sundby, E.; Hoff, B.H. Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine. Molecules 2012, 17, 820-835.

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