Application of 2-amino-6-vinylpurine as an efficient agent for conjugation of oligonucleotides

Md Monsur Ali, Fumi Nagatsugi, Shigeki Sasaki, Ryusuke Nakahara, Minoru Maeda

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Attempts have been made to conjugate a variety of molecules with oligonucleotides to achieve useful functions. In this study, we have established a new efficient method for post-synthetic conjugation of oligonucleotides with the use of the 2-amino-6-vinylpurine nucleoside. Amino nucleophiles form the corresponding conjugates under acidic conditions, whereas thiol nucleophiles reacted efficiently under alkaline conditions. Thus, glutathione and HS-Cys-(Arg) 8 without protecting groups were efficiently conjugated to the 2-amino-6-vinylpurine-bearing ODN under alkaline conditions. The use of 2-amino-6-vinylpurine as an agent for conjugation is advantageous in that it is stable during the reaction and may be applied to conjugation of ODNs with multiple functional molecules.

Original languageEnglish
Pages (from-to)159-169
Number of pages11
JournalNucleosides, Nucleotides and Nucleic Acids
Volume25
Issue number2
DOIs
Publication statusPublished - Jan 1 2006

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Oligonucleotides
Nucleophiles
Bearings (structural)
Molecules
Nucleosides
Sulfhydryl Compounds
Glutathione
2-amino-6-vinylpurine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Genetics

Cite this

Application of 2-amino-6-vinylpurine as an efficient agent for conjugation of oligonucleotides. / Ali, Md Monsur; Nagatsugi, Fumi; Sasaki, Shigeki; Nakahara, Ryusuke; Maeda, Minoru.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 25, No. 2, 01.01.2006, p. 159-169.

Research output: Contribution to journalArticle

Ali, Md Monsur ; Nagatsugi, Fumi ; Sasaki, Shigeki ; Nakahara, Ryusuke ; Maeda, Minoru. / Application of 2-amino-6-vinylpurine as an efficient agent for conjugation of oligonucleotides. In: Nucleosides, Nucleotides and Nucleic Acids. 2006 ; Vol. 25, No. 2. pp. 159-169.
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