Functionalized nucleotides are instrumental in modern nucleic acid biochemistry. Nucleoside triphosphates (dNTPs and NTPs) are involved in various biological processes like neurotransmission, replication, transcription and translation. Various functional group modifications have helped researchers to have an in-depth understanding of nucleic acid structures and functions. Selenium modification of these nucleotides can provide further insight into nucleic acid flexibility, nucleobase pairing/stacking, and duplex recognition/stability. Herein, we report the first chemical synthesis of 6-Se-2'-deoxy-guanosine-5'-triphosphate (6-SedGTP) via a �new synthetic methodology�  developed in Prof. Huang's laboratory. In this strategy, 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one and tri-n-butylammonium pyrophosphate are used to form a triphosphate intermediate which reacts with the nucleoside  to form P2, P3-dioxo-P1-5'-nucleosidylcyclotriphosphite. The product 6-SedGTP being yellow in color offers potential applications as deoxyribonucleic acid (DNA) visualization probe. This Se-modified triphosphate is efficiently recognized by DNA polymerase. The synthetic Se-DNA is highly nuclease-resistant compared to the native. These findings indicate that the modified Se-DNAs have a great potential for nucleic acid based diagnosis and therapeutics.

Synthesis and incorporation of 6-seleno-2'-deoxyguanosine triphosphate into DNA by DNA polymerase

243rd National Meeting (2012)

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