Polymethylene Derivatives of Nucleic Bases Bearing ω-Functional Groups: Х. A Novel Approach to the Synthesis of α-Amino-ω-Nucleo Carboxylic Acids

Abstract

A novel approach to the synthesis of α-amino-ω-nucleo carboxylic acids, analogs of willardiin, an activator of the receptor of α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid, which is responsible for the transfer of a fast stimulating signal in the synapses of the nervous system of vertebrates, is proposed. Based on substantial differences in the reactivity of halogen atoms in α,ω-dihalogen carboxylic acids, the esters of α-phthaloylimido-ω-chloro carboxylic acids have been synthesized. The alkylation of uracil, thymine, and adenine with these esters gave the key compounds, the esters of α-phthaloylimido-ω-nucleo carboxylic acids. The consecutive removal of the phthalyl protective group and acid hydrolysis led to new polymethylene derivatives of nucleic bases, which are α-amino-ω-nucleo carboxylic acids. The physical and chemical properties of these compounds were studied.