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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 from N-acetylcysteine, bovine serum albumin, or human hair (pretreated with a reducing agent to reveal cysteine thiols in ?-keratin). This fluorescence is observable even with micrograms of probe.

SUBMITTER: Patterson AL

PROVIDER: S-EPMC3885416 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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

Patterson Anastasia L AL May Mary D MD Visser Bryan J BJ Kislukhin Alexander A AA Vosburg David A DA

Journal of chemical education 20131201 12

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 <i>N</i>-acetylcysteine, bovine serum albumin, or human hair (pretreated with a ...[more]

PMID: 24415795

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Dataset Information

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

Publications

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

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