dc.contributor.author | Esmurziev, Aslan | |
dc.contributor.author | Reimers, Arne | |
dc.contributor.author | Andreassen, Trygve | |
dc.contributor.author | Simic, Nebojsa | |
dc.contributor.author | Sundby, Eirik | |
dc.contributor.author | Hoff, Bård Helge | |
dc.date.accessioned | 2015-09-30T12:31:10Z | |
dc.date.accessioned | 2015-10-14T07:30:35Z | |
dc.date.available | 2015-09-30T12:31:10Z | |
dc.date.available | 2015-10-14T07:30:35Z | |
dc.date.issued | 2012 | |
dc.identifier.citation | Molecules 2012, 17(1):820-835 | nb_NO |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/11250/2356143 | |
dc.description | - | nb_NO |
dc.description.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. | nb_NO |
dc.language.iso | eng | nb_NO |
dc.rights | Navngivelse 3.0 Norge | * |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/no/ | * |
dc.title | Benzoylated uronic acid building blocks and synthesis of N-uronate conjugates of lamotrigine | nb_NO |
dc.type | Journal article | nb_NO |
dc.type | Peer reviewed | nb_NO |
dc.date.updated | 2015-09-30T12:31:10Z | |
dc.identifier.doi | 10.3390/molecules17010820 | |
dc.identifier.cristin | 905911 | |