The solid phase synthesis of oligonucleotides containing a 3′-peptide moiety

Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

“…In a different approach, Haralambidis et al [77][78][79][80] reported the derivatization of aminopropylated-CPG with the peptide (Ala-Lys-)sAla (as in 52) toward the preparation of peptideoligodeoxyribonucleotide conjugates. This strategy would also permit the attachment of non-radioactive labels to the lysine residues of the conjugates.…”

Polyamide‐oligonucleotide Hybrid Molecules

“…This was to be expected as it is known that the major pathway for oligonucleotide degradation inside cells is through 3'-exonuclease attack, and we know that the conjugate molecules are resistant to 3'-exonucleases e.g. snake venom phosphodiesterase (Haralambidis et al 1987(Haralambidis et al , 1990a. These molecules also showed a specific antisense inhibition of HIV.…”

“…In order to achieve these aims we have recently developed a new type of modified oligonucleotide, in which a polyamide (which can be a peptide) is covalently attached to an oligonucleotide (Haralambidis et al 1987(Haralambidis et al , 1990a. These molecules are prepared by total synthesis and have applications in both of the areas discussed above.…”

New developments in the synthesis of oligonucleotide-peptide conjugates

“…It is known that acidic solutions provoke depurination of purine nucleosides. On the other hand, depurination is slower in oligonucleotides and indeed several experiments on the use of TFA to remove Boc groups in the presence of oligodeoxynucleotides were described almost two decades ago [7,8] . In order to study the extension of this reaction we have treated 4 oligodeoxynucleotide sequences (T 9 , T 4 CT 4 , T 4 AT 4 and T 4 GT 4 ) with 95% TFA aqueous solution.…”