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Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics.

Tatyana V Abramova1, Sergey S Belov2, Yulia V Tarasenko1

  • 1Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave, 8, Novosibirsk 630090, Russia.

Beilstein Journal of Organic Chemistry
|July 4, 2014
PubMed
Summary

A new method for synthesizing morpholinoglycine oligonucleotide (MorGly) mimics using solid-phase synthesis has been developed. This approach utilizes a novel linker and specific nucleoside analogues for efficient peptide synthesis.

Keywords:
labile linkermorpholino oligomersoligonucleotide mimicssolid-phase-supported peptide synthesis (SPPS)

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Oligonucleotide Chemistry

Background:

  • Morpholino oligonucleotide (MOO) analogues are crucial in nucleic acid therapeutics.
  • Solid-phase peptide synthesis (SPPS) is a standard technique for peptide assembly.
  • Developing efficient synthesis routes for modified oligonucleotides is essential for drug discovery.

Purpose of the Study:

  • To develop an efficient solid-phase-supported peptide synthesis (SPPS) for morpholinoglycine oligonucleotide (MorGly) mimics.
  • To introduce a novel labile linker group for improved synthesis control.
  • To utilize 2-aminomethylmorpholino nucleoside analogues as key building blocks.

Main Methods:

  • Solid-phase-supported peptide synthesis (SPPS) was employed.
  • A novel labile linker group incorporating an oxalyl residue was designed and synthesized.
  • 2-aminomethylmorpholino nucleoside analogues were prepared and used as the first subunits.

Main Results:

  • An efficient SPPS strategy for MorGly mimics was successfully established.
  • The novel oxalyl-containing linker demonstrated effective lability under specific conditions.
  • The 2-aminomethylmorpholino nucleoside analogues were efficiently incorporated into the growing peptide chain.

Conclusions:

  • The developed SPPS strategy provides an efficient route for synthesizing MorGly mimics.
  • The novel linker design enhances the utility of SPPS for modified oligonucleotide synthesis.
  • This method facilitates the production of morpholino-based nucleic acid analogues for potential therapeutic applications.