D. Wilson, R. Hurd, K. Keshari
Apr 7, 2009
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Journal
Proceedings of the National Academy of Sciences
Abstract
Emerging fields such as metabolic profiling, the study of the molecular processes and chemical contents of living cells, require new diagnostic tools to identify biomarkers that may have clinical significance. David Wilson et al. developed a method to enhance the nuclear magnetic resonance spectra of biomolecules by using acetic anhydride’s high reactivity with the amine group of amino acids. Prepolarized 13C-labeled acetic anhydride tagged molecules of interest in a few seconds, with the Nacetylation reaction occurring more rapidly than hydrolysis. The authors’ approach resolved mixtures of amino acids in solution, including glycine, serine, valine, leucine, and alanine, with a signal enhancement of up to 1,400-fold in a single pulse, and at physiologic concentrations. The yields for the acetylation reaction ranged up to 97%. Acetic anhydride labeling also tagged larger biomolecules, including an N-acetylated version of lysine, as well as a short peptide corresponding to -melanocyte stimulating hormone, which provokes the release of skin pigments, and N-acetylcysteine, a drug administered intravenously to treat acetaminophen overdose. This research paves the way for faster and higher signal-to-noise spectroscopic methods of obtaining critical clinical information, such as a patient’s disease profile, through metabolic evaluations, according to the authors. — F.A.