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

Authors

Anastasia L. Patterson, University of California, Santa Barbara
Mary D. May, Harvey Mudd College
Bryan J. Visser, Baylor College of Medicine
Alexander A. Kislukhin, University of California - San Diego
David A. Vosburg, Harvey Mudd CollegeFollow

Document Type

Article

Department

Harvey Mudd College, Chemistry (HMC)

Publication Date

Fall 11-8-2013

Abstract

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.

Rights Information

© 2013, ACS Publications

Recommended Citation

“‘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.