Next Article in Journal
Isostreptazolin and Sannaphenol, Two New Metabolites from Streptomyces sannanensis
Previous Article in Journal
Comparative Computational Studies of 3,4-Dihydro-2,6-diaryl-4-oxo-pyrimidine-5-carbonitrile Derivatives as Potential Antinociceptive Agents
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
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 / Revised: 2 January 2012 / Accepted: 4 January 2012 / Published: 16 January 2012
Download PDF [296 KB, uploaded 18 June 2014]   |  

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 (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert