278803-36-4Relevant academic research and scientific papers
Synthesis of biologically active n2-amine adducts of 2'-deoxyguanosine
Bonala,Shishkina,Johnson
, p. 7281 - 7284 (2000)
Several biologically important N2-adducts of 2'-deoxyguanosine (dG) that previously were difficultly accessible, have been synthesized directly by means of the Buchwald-Hartwig reaction. The reaction employed in each case involves the coupling
Chemical synthesis of cross-link lesions found in nitrous acid treated DNA: A general method for the preparation of N2-substituted 2'- deoxyguanosines
Harwood, Eric A.,Hopkins, Paul B.,Sigurdsson, Snorri Th.
, p. 2959 - 2964 (2007/10/03)
Treatment of DNA with nitrous acid results in the formation of DNA-DNA cross-links. Two cross-link lesions have previously been isolated and their structures assigned based on spectroscopic data. The major lesion has been proposed to consist of two deoxyguanosine (dG) nucleosides sharing a common N2 atom (1), while the structure of the minor lesion has been proposed to consist of a common nitrogen atom linking C2 of a dG nucleoside to C6 of deoxyadenosine (2). The chemical synthesis of 1 and 2, utilizing a palladium- catalyzed coupling, is described herein. It is demonstrated that the spectroscopic properties of synthetic 1 are identical to that of lesion 1 obtained from nitrous acid cross-linked DNA, thus providing a proof of its structure. Comparison of the limited spectroscopic data available for lesion 2 originating from nitrous acid cross-linked DNA to synthetic 2 supports its structural assignment. The synthetic approach used for synthesis of 1 and 2 is shown to be a general method for the preparation of a variety of N2- substituted dG nucleosides in good yields.
