Synthesis of Amino Acid-Derived 1,2,3-Triazoles: Development of a Nontrivial Fluorescent Sensor in Solution for the Enantioselective Sensing of a Carbohydrate and Bovine Serum Albumin Interaction
| Autor: | Natalí P. Debia, Bruna S. Martins, Diogo S. Lüdtke, Paulo Fernando Bruno Gonçalves, Diego Alves, Maiara T. Saraiva, Fabiano Severo Rodembusch, Roiney Beal |
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| Rok vydání: | 2018 |
| Předmět: |
Carbohydrates
02 engineering and technology 010402 general chemistry 01 natural sciences Polarizable continuum model Molecule Moiety Animals Bovine serum albumin Amino Acids Fluorescent Dyes chemistry.chemical_classification biology Molecular Structure Chemistry Organic Chemistry Enantioselective synthesis Serum Albumin Bovine Stereoisomerism Triazoles 021001 nanoscience & nanotechnology Combinatorial chemistry Fluorescence 0104 chemical sciences Amino acid Solutions biology.protein Cattle Enantiomer 0210 nano-technology |
| Zdroj: | The Journal of organic chemistry. 83(3) |
| ISSN: | 1520-6904 |
| Popis: | A series of amino acid-derived 1,2,3-triazoles presenting the amino acid and the aromatic moieties connected by a triazole-4-carboxylate spacer is discussed in this work. These compounds were achieved in good yields by organocatalytic enamine–azide [3 + 2] cycloadditions. One of the molecules obtained, bearing a 7-chloroquinoline moiety, was photoactive in the UV-violet region and was successfully employed as a probe for substrate-specific enantiomeric sensing using d-(−)-arabinose and l-(+)-arabinose. The potential application as a fluorescent probe to detect protein in phosphate buffer solution was also explored using as model bovine serum albumin (BSA). The studied compounds presented both suppression and association behavior in the presence of BSA. In addition, theoretical calculations were performed at levels ωB97XD/cc-pVDZ and PBE1PBE/6-311+G(d,p) together with the polarizable continuum model to understand the interaction of the molecules with the enantiomers. |
| Databáze: | OpenAIRE |
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