Abstract
Proteinogenic amino acids were derivatized via coupling reactions with N-hydroxysuccinimide esters of Safirinium dyes. The obtained compounds were fully characterized by 1H and 13C NMR, IR, and ESI-MS spectral techniques. Elemental analysis, as well as the crystal structure analysis of exemplary compounds, were performed. The absorption and fluorescent properties of the obtained derivatives have been systematically investigated. The optical properties and very good water solubility allowed for the development of a simple method for the determination of exemplary amino acids by means of micellar electrokinetic chromatography. Moreover, a new class of fluorescent peptide building blocks comprising a spiro-conjugated Safirinium-proline system was obtained. Due to the presence of a permanent positive charge, Safirinium-amino acid dervatives are potential candidates for signal enhancers in MS proteomic analysis. The applicability of the examined ionization tags in signal enhancement and peptide sequencing was proved. The obtained results provide an experimental basis for the development of a new approach for trace amino acids, peptides, and proteins detection by means of absorption, fluorescence, and mass spectrometry.
Highlights
Fluorescence sensing is one of the most versatile, efficient and extensively used approaches for quantitative detection of analytes in low concentrations
We have reported the synthesis of fluorescent amino acids conjugated with
The tagged compounds were obtained in good yields and their structures were characterized through 1H and Safirinium labelling system is simple in terms of synthetic proceduers and the labeled compounds can be prepared with mild reaction conditions and short reaction times
Summary
Fluorescence sensing is one of the most versatile, efficient and extensively used approaches for quantitative detection of analytes in low concentrations. Fluorescence techniques gave opportunities for fundamental research in biotechnology, microbiology, biochemistry, clinical diagnostics, materials science, analytical and environmental chemistry as well as cell and molecular biology, including monitoring of cellular processes with high-resolution in the realtime. Fluorescence spectroscopy is an important and useful tool of analysis, control, and investigation in many fields relevant to physical, chemical, biological, and medical sciences. It gains widespread attention over other techniques due to its operational simplicity, costeffectiveness, low limits of detection, rapid response time of fluorescence assays, large linear range of analysis, and in situ monitor ability. A large range of organic chemosensors have been developed for convenient, highly selective and sensitive detection of trace amounts of biologically significant species such as amino acids (Cys [13,14,15], Asp [16] or Glu [16]), various metal ions including Hg2+ [17], Ag+ [18], Au3+ [19], Mg2+ [20], Cu2+ [19,21,22], Fe2+
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