97632-73-0Relevant articles and documents
New Labeling Reagents for Alcohols in Fluorescence High-Performance Liquid Chromatography
Takadate, Akira,Irikura, Mitsuru,Suehiro, Tsutomu,Fujino, Hiroyuki,Goya, Shujiro
, p. 1164 - 1169 (2007/10/02)
7-Methoxycoumarin-3 (and 4)-carbonyl azides (I and II) were synthesized as highly sensitive fluorescent labeling reagents for use in high-performance liquid chromatography (HPLC).Treatment of 7-methoxycoumarin-3 (and 4)-carbonyl chlorides with a suspension of activated sodium azide in dry acetone gave I and II in 56percent and 54percent yields, respectively.Compounds I and II reacted with alcohols in dichloromethane to give the corresponding highly fluorescent 7-methoxycoumarin-3 (and 4)-carbamic acid esters (IIIa-e and IVa-g). 4-Amino-7-methoxycoumarin (V), isolated as a by-product on labeling with II, was also obtained by heathing II in tetrahydrofuran.Mixtures of primary and secondary alcohols were labeled with I or II and chromatographed on a reversed-phase HPLC column (mobile phase: methanol-water and methanol-chloroform) with a fluorescence detector.The detection limits of a test sample, cholesterol, were 50 fg and 100 ng/100μl on labeling with I and II, respectively.Keywords--7-methoxycoumarin-3-carbonyl azide; 7-methoxycoumarin-4-carbonyl azide; 7-methoxycoumarincarbamic acid ester; 4-amino-7-methoxycoumarin; fluorescence labeled alcohol; HPLC fluorescence detection; fluorescence quantum yield
