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

Yosuke Taniguchi, Lei Wang, Hidenori Okamura, Shigeki Sasaki

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Article numbere80
JournalCurrent Protocols in Nucleic Acid Chemistry
Volume77
Issue number1
DOIs
Publication statusPublished - Jun 2019

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Oligonucleotides
Pseudouridine
Derivatives
Uracil
Oligodeoxyribonucleotides
Nucleosides
Thymidine
Amines
phosphoramidite
triplex DNA
1-methyluracil

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

Cite this

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abstract = "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.",
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