Synthesis of oligonucleotide-peptide conjugates containing a KDEL signal sequence

Article abstract of DOI:10.1016/S0040-4039(00)61458-2

An improved method of preparation of oligonucleotide-peptide conjugates is described. An oligopeptide containing α and ε-aminogroups is mainly substituted at its α-NH₂ end by ε-maleimidocaproic acid-N-hydroxysuccinimide ester at pH 6.5 for 1 h. The N(α)-maleimidocaproyl-peptide derivative, purified by HPLC, reacts with the thiol group of an oligonucleotide in a 82% yield at pH 7.2. The thiol group is generated in situ by the action of tris(carboxyethyl)phosphine on an oligonucleotide bearing a disulfide bridge.