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Purine Nucleosides Modified At C8 Or C2 Position With (Β-Halo)Vinylsulfone And Β-Ketosulfone Reactive Groups And Their Incorporation Into Dna: Synthesis Of The Organoarsenical Antibiotic Arsinothricin And Polyaromatic Hydrocarbons, Md Abu Hasan Howlader
FIU Electronic Theses and Dissertations
Modified nucleosides gained great attention as potential anticancer and antiviral therapeutics. In this dissertation, synthesis and reactivity of (β-iodovinyl)sulfone and β-ketosulfone groups incorporated into purine nucleosides at C8 or C2 positions and DNA incorporation of their 5' triphosphates have been developed. Moreover, synthesis of novel antibiotic arsinothricin (AST) as well as polycyclic aromatic hydrocarbons (PAHs) have been discussed. The 8-(1-iodo-2-tosylvinyl)-2'-deoxyadenosine and 8-(1-Iodo-2-tosylvinyl)adenosine were synthesized employing iodovinylsulfonation of 8-ethynyl precursors with TsNa/I2/NaOAc. The 8-(β-iodovinyl)sulfonyl-2'-deoxyguanosine was prepared via radical mediated iodovinylsulfonation of 8-ethynyl-2'-deoxyguanosine with TsNHNH2/KI/(BzO)2. Conformationally different C2 substituted isomeric adenosine analogues were prepared by iodovinylsulfonation …