The reaction of nucleophilic species with quinonoid 6,6,7,7-tetramethyldihydropterin

J. B. Noar, U. V. Venkataram, Thomas C. Bruice, G. Bollag, R. Whittle, D. Sammons, R. Henry, Stephen J. Benkovic

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Abstract

The products, kinetics, and mechanisms for the reaction of HO-, NH2OCH3, and HOCl with 1,5-quinonoid 6,6,7,7-tetramethyldihydropterin are provided. The reaction with hydroxide leads to a rearranged imidazolone whose structure was proved by independent synthesis. With methoxylamine the product is a dihydro adduct derived from methoxylamine displacement of the 2-amino group. In this case the structure of the product was obtained via X-ray crystallography and 13C NMR with the former providing novel information about the tautomeric form of this pterin quinonoid species. The chlorination of the quinonoid generates N2 or N3 chloroamines based on high-resolution mass spectrometric analysis. Mechanisms for these transformations are proposed.

Original languageEnglish (US)
Pages (from-to)17-27
Number of pages11
JournalBioorganic Chemistry
Volume14
Issue number1
DOIs
StatePublished - Mar 1986

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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    Noar, J. B., Venkataram, U. V., Bruice, T. C., Bollag, G., Whittle, R., Sammons, D., Henry, R., & Benkovic, S. J. (1986). The reaction of nucleophilic species with quinonoid 6,6,7,7-tetramethyldihydropterin. Bioorganic Chemistry, 14(1), 17-27. https://doi.org/10.1016/0045-2068(86)90014-3