Fluorescence derivatisation of amino acids in short and long-wavelengths

3-(Naphthalen-1-ylamino)propanoic acid was coupled to the amino group of the main and lateral chains of various amino acids in order to evaluate its applicability as a fluorescent derivatising reagent. The resulting amino acid derivatives are strongly fluorescent with a maximum emission of about 415 nm. Condensation of these derivatives with 5-ethylamino-4-methyl-2-nitrosophenol hydrochloride resulted in the corresponding blue benzo[a]phenoxazinium conjugates, also revealing strong fluorescence in ethanol and water at physiological pH and good quantum yields, but with emission wavelengths between 644 and 657 nm, which was preferable in biological assays.