A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates

Article abstract of DOI:10.1016/S0040-4039(99)00748-0

A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH₂CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, ⁵'TGTCGACACCCAATT³'-OPO(OH)OCH₂CH(NH₂)COOH, and a oligonucleotide-peptide conjugate, ⁵'TGTCGACACCCAATT³'- OPO(OH)OCH₂CH(NH₂)CONHCH₂COOH, have been obtained in high purity.