799247-62-4Relevant academic research and scientific papers
Oligonucleotides with 2′-O-carboxymethyl group: Synthesis and 2′-conjugation via amide bond formation on solid phase
Kachalova, Anna,Zubin, Eugeny,Stetsenko, Dmitry,Gait, Michael,Oretskaya, Tatiana
, p. 2793 - 2797 (2004)
An efficient method for synthesis of oligonucleotide 2′-conjugates via amide bond formation on solid phase is described. Protected oligonucleotides containing a 2′-O-carboxymethyl group were obtained by use of a novel uridine 3′-phosphoramidite, where the carboxylic acid moiety was introduced as its allyl ester. This protecting group is stable to the conditions used in solid-phase oligonucleotide assembly, but easily removed by Pd(0) and morpholine treatment. 2′-O-Carboxymethylated oligonucleotides were then efficiently conjugated on a solid support under normal peptide coupling conditions to various amines or to the N-termini of small peptides to give products of high purity in good yield. The method is well suited in principle for the preparation of peptide-oligonucleotide conjugates containing an amide linkage between the 2′-position of an oligonucleotide and the N-terminus of a peptide.
