title: Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories.
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 fromN-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.
authors.affiliation: Department of Chemistry, Harvey Mudd College, Claremont, California 91711, United States.
authors.forename: Anastasia L
authors.initials: AL
authors.lastname: Patterson
authors.affiliation: Department of Chemistry, Harvey Mudd College, Claremont, California 91711, United States.
authors.forename: Mary D
authors.initials: MD
authors.lastname: May
authors.affiliation: Department of Chemistry, Harvey Mudd College, Claremont, California 91711, United States.
authors.forename: Bryan J
authors.initials: BJ
authors.lastname: Visser
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Kislukhin
authors.affiliation: Department of Chemistry, Harvey Mudd College, Claremont, California 91711, United States.
authors.forename: David A
authors.initials: DA
authors.lastname: Vosburg
keywords: NMR Spectroscopy; fluorescence spectroscopy; green chemistry; hands-on learning; laboratory instruction; microscale lab; organic chemistry; organosulfur compounds; second-year undergraduate; synthesis