62906-33-6Relevant academic research and scientific papers
Kinetic and Theoretical Studies on the Mechanism of Alkaline Hydrolysis of DNA
Takeda, Naoya,Shibata, Masahiko,Tajima, Nobuo,Hirao, Kimihiko,Komiyama, Makoto
, p. 4391 - 4396 (2007/10/03)
The reaction mechanism of alkaline hydrolysis of DNA has been investigated by kinetic analysis and density-functional-theory calculation. The rates of hydrolysis of thymidine 3′-monophosphate esters (including thymidylyl(3′-5′)thymidine (Tp-OT)) monotonically decrease as the leaving groups get poorer. According to the theoretical calculation in which the solvent effects are incorporated, no intermediate is formed in the course of the reaction. In the alkaline hydrolysis of the activated Tp-OT analogues having good leaving groups, the 3′,5′-cyclic monophosphate of thymidine is concurrently formed through the intramolecular attack by the 5′-alkoxide ion. In the hydrolysis of the native dinucleotide, however, this side reaction does not occur, since the transition state leading to the departure of its poor leaving group cannot be formed due to conformational restraint. These arguments are supported by the theoretical analysis on the hydrolysis of both dimethyl phosphate and its O(bridging)→S substituted analogue.
Hydrolysis and Methanolysis of the Phenyl Ester of Thymidine 3',5'-Cyclic Monophosphate: pH-Dependent Competition Between PO and CO Bond Ruptures
Oivanen, Mikko,Varila, Jaana,Hankamaki, Teemu,Koole, Leo H.,Lonnberg, Harri
, p. S26 - S29 (2007/10/03)
pH-Rate profiles and product distributions for the hydrolytic reactions of the cis-phenyl ester of thymidine 3',5'-cyclic monophosphate have been determined over the pH-range 0-14.The pH-independent hydrolysis (pH 2-7) of the phosphotriester moiety appears to proceed mainly by cleavage of the C5'O bond, whereas the hydroxide- and hydronium-ion-catalyzed reactions involve rupture of one of the PO bonds.
Synthesis and Properties of S,S-Diaryl Thymidine Phosphorodithioates
Sekine, Mitsuo,Hamaoki, Ken,Hata, Tsujiaki
, p. 3815 - 3827 (2007/10/02)
Appropriately protected and unprotected S,S-diphenyl thymidine 3'- or 5'-phosphorodithioates and S,S-bis(4-methoxyphenyl) thymidine 3'- or 5'-phosphorodithioates were successfully prepared by the reaction of the thymidine derivatives with cyclohexylammoni
