Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules

Naoko Takenaga; Takumi Hayashi; Shohei Ueda; Hiroyuki Satake; Yoichi Yamada; Tetsuya Kodama; And Toshifumi Dohi

doi:10.3390/molecules24173034

Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules

Molecules. 2019 Aug 21;24(17):3034. doi: 10.3390/molecules24173034.

Authors

Naoko Takenaga¹, Takumi Hayashi², Shohei Ueda³, Hiroyuki Satake⁴, Yoichi Yamada⁵, Tetsuya Kodama⁶, And Toshifumi Dohi⁷

Affiliations

¹ Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan. ntakenag@meijo-u.ac.jp.
² College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
³ Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
⁴ Department of Liberal Arts and Sciences, Kanagawa University of Human Services, 1-10-1 Heisei-cho, Yokosuka, Kanagawa 238-8522, Japan.
⁵ School of Pharmacy, Shujitsu University, 1-6-1 Nishigawara, Naka-ku, Okayama 703-8516, Japan.
⁶ Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
⁷ College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan. td1203@ph.ritsumei.ac.jp.

Abstract

Iodonium(III) salts bearing uracil moieties have recently appeared in the literature, but their structural scope and utilization are limited because of their hygroscopic characteristics. In this study, we describe our detailed investigations for synthesizing a series of uracil iodonium(III) salts derived with various structural motifs and counterions. These new compounds have been utilized as attractive synthetic modules in constructing functionalized nucleobase and nucleosides.

Keywords: hypervalent compound; iodonium salt; nucleobase; uracil.

MeSH terms

Molecular Structure
Nucleosides / chemistry
Onium Compounds / chemistry*
Uracil / chemistry*

Substances

Nucleosides
Onium Compounds
Uracil

Abstract

MeSH terms

Substances

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