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 language | English |
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Pages (from-to) | 801-804 |
Number of pages | 3 |
Journal | Bioorganic and Medicinal Chemistry Letters |
Volume | 14 |
Issue number | 3 |
DOIs | |
Publication status | Published - 9 Feb 2004 |
Keywords
- Conjugate
- Oligonucleotide
- Peptide