Syntheses and electrochemical properties of novel aminopyrimidinone derivatives as a new class of abasic-site binders
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We describe syntheses and electrochemical properties of a new class of aminopyrimidinone derivatives: 2-amino-4-(3′,4′-dimethoxyphenyl)-6-pyrimidinone, 2-amino-4-(3′,4′-dihydroxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3′,4′-dimethoxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3′,4′-dihydroxyphenyl)-6-pyrimidinone, and 4-amino-5-(3′,4′-dihydroxyphenyl)-2,6-pyrimidinione, three of which possess a catechol unit as an oxidation-active moiety for developing electrochemically detectable abasic-site binders. These compounds were synthesized via a pyrimidine-ring forming reaction with guanidine. Cyclic voltammetry measurements revealed that the catechol-bearing derivatives showed oxidation potentials lower than that of DNA, indicating that they satisfied the requirements for the purpose.
KeywordsElectrochemistry Abasic site Aminopyrimidinone Catechol
- 9.H. Abe, M. Takase, Y. Doi, S. Matsumoto, M. Furusyo, M. Inouye, Eur. J. Org. Chem. 2005, 2931 (2005)Google Scholar