Sensitive derivatization reagents for hydroxyl and amino compounds for thin-layer or high-performance liquid chromatography with fluorescence detection

✍ Scribed by Yasuto Tsuruta; Kazuya Kohashi

• Book ID: 104100268
• Publisher: Elsevier Science
• Year: 1987
• Tongue: English
• Weight: 329 KB
• Volume: 192
• Category: Article
• ISSN: 0003-2670
• DOI: 10.1016/s0003-2670(00)85716-5

✦ Synopsis

Three fluorescent derivatization reagents for compounds having hydroxyl and/or amino groups are described. 4-( 2-Phthalimidyl)benzoyl chloride, 3-( 2-phthalimidyl)benzoyl chloride and 3-( 2-phthalimidyl)4-methoxybenzoyl chloride, prepared from the corresponding phthalimidylbenzoic acid, were stable at room temperature and condensed quantitatively with alcohols, amines and amino acids in the presence of alkali under mild conditions to give strongly fluorescent derivatives. The derivatives were separated by thin-layer and high-performance liquid chromatography.

Benzoyl chloride, 4-nitrobenzoyl chloride and 3,5dinitrobenzoyl chloride have been widely used for derivatization of alcohols and amines, and applied in quantitative liquid chromatography with U.V. detection [l, 21. However, these conventional reagents were considered to lack either stability or sensitivity in certain instances, and have been replaced by highly sensitive fluorescent derivatization reagents [ 31.

Some phthalimidylbenzoyl chlorides (phibyl-Cl: I, II and III) were found to be stable at room temperature and to be rapid and quantitative fluorescent derivatizing agents for alcohols, amines and amino acids. The present communication deals with the preparation of these three reagents, having both a fluorophore and a benzoyl chloride group, and their applicability to labelling of hydroxyl and amino compounds for thin-layer chromatography (t.1.c.) and high-performance liquid chromatography (h.p.1.c.) with fluorescence detection.