Among the variety of nucleic acid modifications, alkylation at the N3-site of purines such as adenosine, plays a critical role in the processing of genomic information. However, a direct evaluation of the outcomes of adenosine modification at the N3-site is compromised by N3-alkylation-driven depurination of DNA. Recently, we described a general strategy for the synthesis of 3-deaza-3-alkyl-adenine and adenosine derivatives. The resulting 3-deaza-3-alkyl-adenosine phosphoramidites were incorporated into oligonucleotides, and the influence of 3-alkyl group was investigated through DNA duplex thermal stability studies. We assessed the impact of DNA minor groove alkylation on the replication and transcription processes using primer extension assay with human DNA and RNA polymerases.<br/>

Modified 3-deaza-3-alkyl-adenosines as minor groove alkylation mimics in translesion DNA synthesis

256th National Meeting (2018)

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