Syntheses and electrochemical properties of novel aminopyrimidinone derivatives as a new class of abasic-site binders

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. Graphical Abstract: [Figure not available: see fulltext.]