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Open AccessArticle

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

1
Norwegian University of Science and Technology (NTNU), Høgskoleringen 5, Trondheim NO-7491, Norway
2
Sør-Trøndelag University College, E.C. Dahls Gate 2, Trondheim NO-7004, Norway
3
Department of Neuroscience, Faculty of Medicine, Norwegian University of Science and Technology (NTNU), Trondheim NO-7491, Norway
4
Department of Biotechnology, Norwegian University of Science and Technology (NTNU), Trondheim NO-7491, Norway
*
Author to whom correspondence should be addressed.
Molecules 2012, 17(1), 820-835; https://doi.org/10.3390/molecules17010820
Received: 7 December 2011 / Revised: 2 January 2012 / Accepted: 4 January 2012 / Published: 16 January 2012
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. View Full-Text
Keywords: uronic acid building blocks; lamotrigine-N2-glucuronide; fluorinated carbohydrates uronic acid building blocks; lamotrigine-N2-glucuronide; fluorinated carbohydrates
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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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