| Benzoylated uronic Acid building blocks and synthesis of N-uronate conjugates of lamotrigine. | |
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MedLine Citation:
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PMID: 22269868 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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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. |
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Authors:
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Aslan M Esmurziev; Arne Reimers; Trygve Andreassen; Nebojsa Simic; Eirik Sundby; Bård Helge Hoff |
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Publication Detail:
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Type: Journal Article Date: 2012-01-16 |
Journal Detail:
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Title: Molecules (Basel, Switzerland) Volume: 17 ISSN: 1420-3049 ISO Abbreviation: Molecules Publication Date: 2012 |
Date Detail:
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Created Date: 2012-01-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100964009 Medline TA: Molecules Country: Switzerland |
Other Details:
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Languages: eng Pagination: 820-35 Citation Subset: IM |
Affiliation:
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Norwegian University of Science and Technology (NTNU), Høgskoleringen 5, Trondheim NO-7491, Norway. eirik.sundby@hist.no. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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