NMR Characterization of Products Formed in Diazotizing Mixtures of Luminol and 3-Amino-L-Tryosine
Abstract
A diazotized mixture of luminol and 3-amino-L-tyrosine prepared as an acetone-precipitated solid polymerizes slowly (over a period of weeks) yielding a brown, water soluble polymer which migrates electrophoretically as an anion at pH 6. Solutions of this substance in Heavy water or a mixed D2O/deuterated Dimethylsulfoxide solvent present very broadened 1 Hydrogen-nmr resonances, and all attempts to chemically fragment this material into its subunit structures have been unsuccessful. The polymer, which has been named diazoluminomelanin (DALM) because of a possible relationship to the natural melanins, is of interest because its aqueous solution with alkaline Hydrogen peroxide and bicarbonate ion flashes a transient chemiluminescence on being irradiated with an intense pulse of microwave energy. Also, aqueous solutions of DALM serve as substrates for the green heme proteins. The reactions leading to DALM appear to involve chiefly 3-diazonium-L-tyrosine and the 5-diazonium derivative of luminol combined in an intimate solid matrix. This solid presents a strong esr absorption, and the polymerization may involve both homolytic and heterolytic processes. Characterization of a polymer obtained from diazotized aqueous solutions of 3-amino-L-tyrosine alone indicate a linkage based on displacement of the 3-diazonium group by the alpha-amino nitrogen atom, i.e., an aryl amine polymer which retains the structural qualities of 3-amino-L-tyrosine.
Document Details
- Document Type
- Technical Report
- Publication Date
- Aug 25, 1991
- Accession Number
- ADA240009
Entities
People
- John R. Wright