Synthesis of 2′-deoxy-4-aminopyridinylpseudocytidine Derivatives for Incorporation Into Triplex Forming Oligonucleotides

Yosuke Taniguchi, Lei Wang, Hidenori Okamura, Shigeki Sasaki

研究成果: ジャーナルへの寄稿学術誌査読

抄録

This unit describes the detailed synthetic protocol for the preparation of the phosphoramidite units of the 2′-deoxy-4-aminopyridinylpseudocytidine derivatives. These C-nucleoside derivatives are useful units for the incorporation into triplex forming oligonucleotides (TFOs) to form the stable triplex DNA containing the CG interrupting sites. Commercially available 1-methyl-2′-deoxypseudouridine is prepared from thymidine and 5-iodo-uracil by a simple method, that is, coupling of glycal and 5-iodo-1-methyluracil by the Heck reaction, followed by desilylation and diastereoselective reduction. The carbonyl group at the 4 position of the pseudouridine derivative is activated by 3-nitorotriazole and treated with the corresponding aromatic amine compounds to produce the 2′-deoxy-4-aminopyridinylpseudocytidine derivatives. These derivatives are then successfully converted to the phosphoramidite units and incorporated into the oligodeoxynucleotides.

本文言語英語
論文番号e80
ジャーナルCurrent Protocols in Nucleic Acid Chemistry
77
1
DOI
出版ステータス出版済み - 6月 2019

!!!All Science Journal Classification (ASJC) codes

  • 生化学
  • 有機化学

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