We synthesized eight fluorine-containing derivatives of asocorbic acid (AsA) and examined for phage-inactivating effect using nine phages. 2,6-Bis-O-perfluorooctanoyl-AsA (8) and 2,6-bis-O-(7,H-dodecafluoroheptanoyl)-AsA (12) exhibited 3〜8 times greater effect than AsA. The reaction mechanism of the phage-inactivating effect of 8 and 12 was investigated. Bubbling oxygen through the reaction mixture enhanced the inactivation. Bubbling nitrogen through the reaction mixture inhibited the inactivation. Addition to the reaction mixture of H_2O_2 and transition metal ions enhanced the inactivation. Addition of reducing agents, chelating agents and radical scavengers inhibited the inactivation. The findings indicate that the phage-inactivating effect is associated with free radical mechanism due to reactive oxygen species. The increase in the inactivating effect can be attributed to the introduction at C(2) and C(6) of substituents containing highly electronegative fluorine.
