Chemical Synthesis and Stability of Oligonucleotides Modified by Alkyl- or Alkoxy- on the Phosphonates

Chem. J. Chinese Universities

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Chemical Synthesis and Stability of Oligonucleotides Modified by Alkyl- or Alkoxy- on the Phosphonates

LIANG Yuan-Jun, HE Jun-Lin, XU Liang, ZHANG Di, LIU Ke-Liang

Beijng Institute of Pharmacology and Toxicology, The Academy of Military Medical Sciences, Beijing 100850, China

Received:2006-03-20 Revised:1900-01-01 Online:2007-03-10 Published:2007-03-10
Contact: LIU Ke-Liang

Abstract

Abstract: Four novel phosphoramidites with isopentyl, phenethyl, isopentoxy, phenethoxy attached to the phosphorus residue were synthesized through Grignard reaction or a sequential three-step substitution on PCl₃ respectively. Four model oligonucleotides(5'-dTTT_x TT-3', where T_x was formed by introducing each of the novel phosphoramidites above-mentioned) were prepared with high coupling yields to study the compatibility of the new building blocks to the customized DNA/RNA synthesis, and the stability of the oligonucleotides were tested under four kinds of deprotection conditions. Based on HPLC analysis and MALDI-TOF-MS measurement, the fast-deprotection strategy(concentrated ammonia, room temperature, 4 h) was suitable for the solid-phase synthesis of oligonucleotides containing above new building blocks. Undoubtedly, these novel phosphoramidites could be used as the building blocks for nucleic acids research.

Key words: Alkylation modification, Phosphoramidite monomer, Oligonucleotide, HPLC, Stability

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LIANG Yuan-Jun, HE Jun-Lin, XU Liang, ZHANG Di, LIU Ke-Liang. Chemical Synthesis and Stability of Oligonucleotides Modified by Alkyl- or Alkoxy- on the Phosphonates[J]. Chem. J. Chinese Universities, doi: .

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Chemical Synthesis and Stability of Oligonucleotides Modified by Alkyl- or Alkoxy- on the Phosphonates

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