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Synthesis and Structural Characterization of 2'-Deoxy-2'-fluoro-l-uridine Nucleic Acids.

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Despite the development of artificial l-RNA/DNA as therapeutic molecules, the in-depth investigation on their chemical modifications is still limited. Here, we synthesize a chemically derivatized 2'-deoxy-2'-fluoro-l-uridine building block and incorporate… Click to show full abstract

Despite the development of artificial l-RNA/DNA as therapeutic molecules, the in-depth investigation on their chemical modifications is still limited. Here, we synthesize a chemically derivatized 2'-deoxy-2'-fluoro-l-uridine building block and incorporate it into oligonucleotides. Our thermo-denaturization and enzymatic digestion experiments reveal their superior stability. Furthermore, one crystal structure of l-type fluoro-DNA is determined to characterize its handedness. Our results reveal the increase of l-helix stability by fluoro-modification and provide the foundation for its future functional application.

Keywords: deoxy fluoro; synthesis structural; fluoro uridine; fluoro; characterization deoxy; structural characterization

Journal Title: Organic letters
Year Published: 2021

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