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 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.
Received: 7 December 2011; in revised form: 2 January 2012 / Accepted: 4 January 2012 / Published: 16 January 2012
PDF Full-text Download PDF Full-Text [296 KB, uploaded 16 January 2012 11:38 CET]
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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

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.

AMA Style

Esmurziev AM, Reimers A, Andreassen T, Simic N, Sundby E, Hoff BH. Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine. Molecules. 2012; 17(1):820-835.

Chicago/Turabian Style

Esmurziev, Aslan M.; Reimers, Arne; Andreassen, Trygve; Simic, Nebojsa; Sundby, Eirik; Hoff, Bård Helge. 2012. "Benzoylated Uronic Acid Building Blocks and Synthesis of N-Uronate Conjugates of Lamotrigine." Molecules 17, no. 1: 820-835.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert