4.6 Article

A New Ir-NHC Catalyst for Signal Amplification by Reversible Exchange in D2O

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 27, 页码 9277-9282

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201601211

关键词

biocompatible; carbenes; ligand design; parahydrogen; SABRE; water-soluble

资金

  1. European Union
  2. Province of Gelderland (NL) through the EFRO Ultrasense NMR project
  3. Province of Overijssel (NL) through the EFRO Ultrasense NMR project
  4. Deutsche Forschungsgemeinschaft (DFG) [BL 231/47-1]

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NMR signal amplification by reversible exchange (SABRE) has been observed for pyridine, methyl nicotinate, N-methylnicotinamide, and nicotinamide in D2O with the new catalyst [Ir(Cl)(IDEG)(COD)] (IDEG=1,3-bis(3,4,5-tris(diethyleneglycol)benzyl)imidazole-2-ylidene). During the activation and hyperpolarization steps, exclusively D2O was used, resulting in the first fully biocompatible SABRE system. Hyperpolarized H-1 substrate signals were observed at 42.5 MHz upon pressurizing the solution with parahydrogen at close to the Earth's magnetic field, at concentrations yielding barely detectable thermal signals. Moreover, 42-, 26-, 22-, and 9-fold enhancements were observed for nicotinamide, pyridine, methyl nicotinate, and N-methylnicotinamide, respectively, in conventional 300 MHz studies. This research opens up new opportunities in afield in which SABRE has hitherto primarily been conducted in CD,OD. This system uses simple hardware, leaves the substrate unaltered, and shows that SABRE is potentially suitable for clinical purposes.

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