Abstract
Oligonucleotides constitute a class of potential therapeutic agents. Improvement of certain properties, such as cell-specific delivery, cellular uptake efficiency, intracellular distribution, and target specificity can be accomplished by covalent association to peptides [1], Rather than forming ionic oligonucleotide-peptide complexes, covalent association results in more consistent products, in which the desired properties can be controlled by structural variations. We present in this paper a novel methodology for the site-specific ligation of oligonucleotides to peptides through a hydrazone link (Figure 1) [2].
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This ligation strategy was found to be very efficient in the context of one-pot double ligation reactions (synthesis of antigen-bearing glycodendrimers), for the elaboration of peptide-peptide constructs or for the synthesis of lipopeptides. (a) Grandjean, C., Rommens, C., Gras-Masse, H., Melnyk, O. Angew. Chem., Int. Ed. 39, 1068–1071. (b) Bonnet, D., Bourel, L., Gras-Masse, H., Melnyk, O. Tetrahedron Lett. 41, 10003–10007 (2000). (c) Melnyk, O., Fruchart, J.-S., Grandjean, C., Gras-Masse, H. J. Org. Chem., in press (2001).
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Bonnet, D., Ollivier, N., Gras-Masse, H., Melnyk, O. J. Org. Chem. 66, 443–449 (2001).
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Melnyk, O., Ollivier, N., Olivier, C., Gouyette, C., Huynh-Dinh, T., Gras-Masse, H. (2001). Synthesis of Oligodeoxynucleotide-Peptide Conjugates Using Hydrazone Chemical Ligation. In: Lebl, M., Houghten, R.A. (eds) Peptides: The Wave of the Future. American Peptide Symposia, vol 7. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0464-0_48
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DOI: https://doi.org/10.1007/978-94-010-0464-0_48
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