Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories

• Autores: Anastasia L. Patterson, Mary D. May, Bryan J. Visser, Alexander A. Kislukhin, David A. Vosburg
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 90, Nº 12, 2013, págs. 1685-1687
• Idioma: inglés
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• Resumen

  • A green organic laboratory experiment was developed in which students synthesize a sensor for thiols using a microscale, solventless Diels–Alder reaction at room temperature or 37 °C. The molecular probe is easily purified by column chromatography in a Pasteur pipet and characterized by thin-layer chromatography and NMR spectroscopy. The thiol-reactive sensor becomes intensely fluorescent upon exposure to thiols from N-acetylcysteine, bovine serum albumin, or human hair (pretreated with a reducing agent to reveal cysteine thiols in α-keratin). This fluorescence is observable even with micrograms of probe.