Abstract
Conjugation of ethylenediaminetetra-acetic acid (EDTA) to methyl tyrosinate generates a chelating peptoid EDTA bis-(methyl tyrosinate), (EBMT). Peroxynitrite-mediated nitration was studied for the free peptoid and its ferric and cupric complexes. The nitration products were monitored by electronic absorption spectroscopy at λ max of 420 nm (mono-nitrated) and 440 nm (di-nitrated). Peak deconvolution was effected by pH manipulation as the mono-nitrated analogue of tyrosine exhibited a bathochromic shift from 365 nm (below its p K a of 6.8) to 420 nm. Rates of nitration were: free peptoid <Cu(II) complex <<Fe(III) complex. These results demonstrate the potential of EBMT to act as a radical scavenging chelating peptoid antioxidant.
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