A novel synthesis of oligonucleotide-peptide conjugates with a base- labile phosphate linker between the two components according to the allyl- protected phosphoramidite strategy

Akira Sakakura, Yoshihiro Hayakawa

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

An efficient synthesis of base-labile nucleotide-peptide conjugates has been accomplished, in which the two components are directly linked between the terminal hydroxyl of a nucleotide and the hydroxyl of a serine or threonine residue of a peptide by a phosphodiester bond. This synthesis utilizes the phosphoramidite method with allyl for the phosphate linkages and the C-terminal of the peptide and allyloxycarbonyl for the nucleoside bases and the N-terminal of the peptide. In this synthesis, the removal of the allylic protecting groups and the detachment of the products was achieved under non-basic or mild basic conditions to bring about no conspicuous decomposition of the labile phosphate linker, and thus the target conjugates were obtained at a high purity and in high yields. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4427-4435
Number of pages9
JournalTetrahedron
Volume56
Issue number26
Publication statusPublished - Jun 23 2000
Externally publishedYes

Fingerprint

Oligonucleotides
Phosphates
Peptides
Hydroxyl Radical
Nucleotides
Threonine
Nucleosides
Serine
Decomposition
phosphoramidite

Keywords

  • Nucleic acid analogs
  • Peptide analogs
  • Phosphoramidites
  • Solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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AB - An efficient synthesis of base-labile nucleotide-peptide conjugates has been accomplished, in which the two components are directly linked between the terminal hydroxyl of a nucleotide and the hydroxyl of a serine or threonine residue of a peptide by a phosphodiester bond. This synthesis utilizes the phosphoramidite method with allyl for the phosphate linkages and the C-terminal of the peptide and allyloxycarbonyl for the nucleoside bases and the N-terminal of the peptide. In this synthesis, the removal of the allylic protecting groups and the detachment of the products was achieved under non-basic or mild basic conditions to bring about no conspicuous decomposition of the labile phosphate linker, and thus the target conjugates were obtained at a high purity and in high yields. (C) 2000 Elsevier Science Ltd.

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