Synthesis of oligonucleotide 2′-conjugates via amide bond formation in solution

Anna V. Kachalova, Dmitry A. Stetsenko, Michael J. Gait, Tatiana S. Oretskaya

    Research output: Contribution to journalArticlepeer-review

    Abstract

    An efficient method for synthesis of 2′-O-carboxymethyl oligonucleotides is described. Fully deprotected oligonucleotides containing a carboxymethyl group at the 2′-position of sugar residue were obtained by a two-step procedure by periodate cleavage of an oligonucleotide containing 1,2-diol group followed by oxidation of the 2′-aldehyde resulted with sodium chlorite. 2′-O-Carboxymethyl oligonucleotides prepared were efficiently coupled in aqueous solution in the presence of a water-soluble carbodiimide to a number of amino acid derivatives or short peptides to afford novel 2′-conjugates of high purity in good yield. The method is thus shown to be suitable in principle for preparation of oligonucleotide-peptide conjugates containing an amide linkage between the 2′-carboxy group of a modified oligonucleotide and the amino terminus of a peptide. © 2003 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)801-804
    Number of pages3
    JournalBioorganic and Medicinal Chemistry Letters
    Volume14
    Issue number3
    DOIs
    Publication statusPublished - 9 Feb 2004

    Keywords

    • Conjugate
    • Oligonucleotide
    • Peptide

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