NMR Studies of Drugs. Applications of Achiral and Chiral Lanthanide Shift Reagents to Acifran Methyl Ester. LSR Binding to a Multifunctional Substrate.
作者:
Lovett Gray,
Robert Rothchild,
期刊:
Spectroscopy Letters
(Taylor Available online 1994)
卷期:
Volume 27,
issue 7
页码: 935-954
ISSN:0038-7010
年代: 1994
DOI:10.1080/00387019408006643
出版商: Taylor & Francis Group
关键词: Europium;LSR;Eu (FOD)3;Eu (HFC)3;Eu (FACAM)3;4,5-Dihydro-5-methyl-4-oxo-5-phenyl-2-furancarboxylic acid methyl ester;Antihyperlipoproteinemic;Enantiomeric excess;Lanthanide-induced shifts;Analysis;Stereoisomer.
数据来源: Taylor
摘要:
The antihyperlipoproteinemic agent, acifran, has been studied as its racemic methyl ester,1, by 60 MHz1H NMR in CDC13solution at 28±1° with the added achiral lanthanide shift reagent (LSR), tris(6, 6, 7, 7, 8, 8, 8-heptaf luoro-2, 2-dimethyl-3, 5-octanedionato-europium(III), Eu (FOD)3,2, for spectral simplification, and with the chiral LSRs, tris[3-(heptafluoropropylhydroxymethylene)-(+)-camphorato]europium(III), Eu(HFC)3,3, and tris[3-(trifluoromethylhydroxymethylene)-(+)-camphorato]europium(III), Eu (FACAM)3,4, for potential determinations of enantiomeric excess. Relative lanthanide-induced shift (LIS) magnitudes with the three LSRs were interpreted as consistent with major lanthanide binding at the 4-oxo carbonyl, but contrasting behavior in observed enantiomeric shift differences (ΔΔδ) with3versus4may suggest different bound complex geometries for3or4with1.
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