Alkylated nucleotides structure

Alkylation reactions are not only of use in structural studies but also provide the basis for the action of a large class of mutagenic compounds.528 Treatment of a nucleoside, nucleotide, or nucleic acid with an alkyl iodide or a dialkylsulfate converts residues of guanosine to an N7-alkyl-guanosine (Eq. 5-18). 

There is one literature report of a much more complex structure containing the 1,3,5-diazaphosphorine ring system (70IZV2254). Compound 71 was prepared during the course of a synthesis of nucleotide analogues containing a C—P bond in the N-alkyl chain. 

FIGURE 50.4. Sulfur mustard, its structure, mechanism of action, and targets of adduct formation. A Mechanism of reaction of sulfur mustard and nucleotide guanine. B Sites of alkylation hy sulfur mustard. Arrows mark identified targets in nucleotides and amino acid histidine. 

Purpose. DNA adducts are nucleotide bases (i.e., purines and pyrimidines) that have been covalently modified by reactive electrophilic chemical intermediates or free radicals. The chemical structures of DNA adducts are diverse and vary from simple alkyl adducts induced by alkylating agents to complex bulky adducts such as those resulting from metabolic activation of polycyclic aromatic hydrocarbons, aromatic amines, and aflatoxins (Dipple 1995 Chiarelli and Jackson 1992 Rundle 2006 Xue and Warshawsky 2005). The purpose of measuring DNA adducts is to determine whether a DNA-reactive compound or a metabolically activated... 

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