Ligand Exchange/Scrambling Study of Gold(I)-Phosphine Complexes in the Solid Phase by DESI-MS Analysis
- University of Sargodha, Department of Chemistry (Pakistan)
- Illinois State University, Department of Chemistry (United States)
- LCW University, Department of Chemistry (Pakistan)
- Florida Gulf Coast University, Department of Chemistry and Physics (United States)
Only a few analytical techniques are available for the characterization of mechanochemical synthetic reaction products. We demonstrate here that DESI-MS is a powerful technique for this purpose, combining the selectivity of MS-based assays with the simplicity and in situ analysis capability of ambient ionization methods. In this work, we report that auranofin, a gold-based drug, and its precursor triethylphosphine gold(I) chloride undergo a complex array of ligand exchange/scrambling reactions with thiol-containing amino acids in the solid state. The products were readily characterized by DESI-MS analysis from the solid-phase reaction, clearly exhibiting ligand exchange and scrambling, with independent confirmation by solid state {sup 13}C-NMR. The thioglucose and triethylphosphine moieties exchanged with cysteine and its derivatives, whereas the glutathione replaced 2,3,4,6-tetra-O-acetyl-β-1-D-glucopyranose only. It was concluded that ligand exchange and scrambling reactions can be carried out in the solid state, and some of the unique products reported in this study can be conveniently prepared through mechanochemical synthesis in good yields (> 98%), as demonstrated by synthesis of (L-cysteinato-S)-triethylphosphine gold(I) from triethylphosphine gold(I) chloride and L-cysteine. .
- OSTI ID:
- 22925043
- Journal Information:
- Journal of the American Society for Mass Spectrometry, Vol. 30, Issue 11; Other Information: Copyright (c) 2019 American Society for Mass Spectrometry; Country of input: International Atomic Energy Agency (IAEA); ISSN 1044-0305
- Country of Publication:
- United States
- Language:
- English
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