Abstract
Oligonucleotide analogues containing one or a few glycine, L-, and D-alanine residues instead of phosphodiester internucleotide linkages were synthesized (C3′-NH-C(O)-CH(X)-NH-C(O)-C4′, where X = H, (S)-CH3, and (R)-CH3. The stability of the duplexes of modified oligonucleotides with their wild-type complements was studied. The incorporation of glycine and L-alanine residues into internucleotide linkages was shown to noticeably decrease the stability of modified duplexes as compared to that of native ones (ΔT m∼−2°C per modification), whereas analogues containing D-alanine linkers form duplexes with increased stability (ΔT m∼+2°C per modification).
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Abbreviations
- DIPEA:
-
diisopropylethylamine
- BDP:
-
1-benztriazolyldiethylphosphate
- BAIB:
-
bis(acetoxy)iodobenzene
- TEMPO:
-
2,2,6,6,-tetramethylpiperidine-1-oxyl
- THF:
-
tetrahydrofuran
- TBAF:
-
tetrabutylammonium fluoride
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Original Russian Text © A.M. Varizhuk, S.V. Kochetkova, N.A. Kolganova, E.N. Timofeev, V.L. Florentiev, 2010, published in Bioorganicheskaya Khimiya, 2010, vol. 36, No. 4, pp. 570–573.
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Varizhuk, A.M., Kochetkova, S.V., Kolganova, N.A. et al. Oligonucleotides containing a peptide internucleotide linkage. A novel class of modified oligonucleotides. Russ J Bioorg Chem 36, 528–531 (2010). https://doi.org/10.1134/S1068162010040138
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DOI: https://doi.org/10.1134/S1068162010040138