Document Detail

Benzoylated uronic acid building blocks and synthesis of N-uronate conjugates of lamotrigine.
MedLine Citation:
PMID:  22269868     Owner:  NLM     Status:  MEDLINE    
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 CdCO(3) 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.
Aslan M Esmurziev; Arne Reimers; Trygve Andreassen; Nebojsa Simic; Eirik Sundby; Bård Helge Hoff
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2012-01-16
Journal Detail:
Title:  Molecules (Basel, Switzerland)     Volume:  17     ISSN:  1420-3049     ISO Abbreviation:  Molecules     Publication Date:  2012  
Date Detail:
Created Date:  2012-01-24     Completed Date:  2012-09-18     Revised Date:  2013-08-21    
Medline Journal Info:
Nlm Unique ID:  100964009     Medline TA:  Molecules     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  820-35     Citation Subset:  IM    
Norwegian University of Science and Technology (NTNU), Trondheim, Norway.
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MeSH Terms
Benzene / chemistry*
Candida / metabolism
Ethanol / metabolism
Magnetic Resonance Spectroscopy
Triazines / chemical synthesis*,  chemistry
Uronic Acids / chemical synthesis,  chemistry*
Reg. No./Substance:
0/Triazines; 0/Uronic Acids; 133310-19-7/lamotrigine 2-N-glucuronide; 64-17-5/Ethanol; 71-43-2/Benzene; U3H27498KS/lamotrigine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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