Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories
Harvey Mudd College, Chemistry (HMC)
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.
© 2013, ACS Publications
“‘Solvent-free synthesis and fluorescence of a thiol-reactive sensor for undergraduate organic laboratories,” Patterson, A.L.; May, M.D.; Visser, B.J.; Kislukhin, A.A.; Vosburg, D.A. J. Chem. Educ. 2013, 90, 1685-1687.