The discovery of the bacteria strain GFAJ-1, reportedly able to substitute Arsenic for Phosphorous in deoxyribonucleic acid polymers, has been met with controversy including the chemical stability of an arsenate diester linkage in a DNA backbone. We report here synthetic methods to synthesize dinucleotides connected with an arsenate diester backbone for the study of hydrolysis rates of these arsenate diester linkages in DNA. Our synthetic methodology for the synthesis of arsenate diester linkages between two thymidine analogs included arsenite chemistry, similar to phosphoramidite chemistry used in oligonucleotide synthesis, and arsenate chemistry employing the SN2 displacement of activated 5' and 3' thymidine derivatives. We are currently investigating the kinetics of hydrolysis of these species.

Synthesis of arsenate diester internucleotide linkages

243rd National Meeting (2012)

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