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Biochimica et biophysica acta

Highly site-specific oxygenation of 1-methylhistidine and its analogue with a copper (II)/ascorbate-dependent redox system.


PMID 2364090

Abstract

The reaction of histidine-related materials with copper(II) and ascorbate under physiological conditions has been studied chemically. We discovered that 1-methylimidazole and its analogues, including biological metabolites L-1-methylhistidine and anserine (beta-alanyl-L-1-methylhistidine), exhibited dramatic reactivity with copper(II)/ascorbate. Reaction of copper(II) and ascorbate occurs specifically at the C-2 position of the imidazole ring of L-1-methylhistidine and anserine derivatives with mono-oxygenation to give the 1-methyl-2-imidazolones in good to excellent yields (70-80%). The occurrence of an oxocopper(III) intermediate in the oxidation process of ascorbate is postulated.

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67520
1-Methyl-L-histidine, ≥98.0% (TLC)
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