Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 13, Pages 3396-3399Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310284
Keywords
cysteine; long-lived spin states; NMR spectroscopy; parahydrogen; thiol conjugate addition
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Funding
- NSF [CHE-0848234, CHE-0957586]
- US National Science Foundation [CHE0116222]
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Nuclear magnetic resonance (NMR) spectroscopy and magnetic resonance imaging (MRI) have become important techniques in many research areas. One major limitation is the relatively low sensitivity of these methods, which recently has been addressed by hyperpolarization. However, once hyperpolarization is imparted on a molecule, the magnetization typically decays within relatively short times. Singlet states are well isolated from the environment, such that they acquire long lifetimes. We describe herein a model reaction for read-out of a hyperpolarized long-lived state in dimethyl maleate using thiol conjugate addition. This type of reaction could lend itself to monitoring oxidative stress or hypoxia by sensitive detection of thiols. Similar reactions could be used in biosensors or assays that exploit molecular switching. Singlet lifetimes of about 4.7min for H-1 spins in [D-4]MeOH are seen in this system.
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