The
formation of N-methoxyoxazolidines in the
preparation of oligonucleotide–peptide conjugates was evaluated.
The reaction occurred between unprotected 2′-N-(methoxy)amino-modified oligonucleotides and peptide aldehydes in
reasonable yields when isolated. The reaction is reversible under
slightly acidic conditions, and it is pH-responsive. The rate and
the equilibrium constant may be varied with structurally different
aldehydes, allowing an optimization of the ligation and cleavage rate
of the resultant conjugates. Therefore, this concept can be considered
a cleavable linker.
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