A1 Refereed original research article in a scientific journal
Conjugation of Oligonucleotides to Peptide Aldehydes via a pH-Responsive N-Methoxyoxazolidine Linker
Authors: Aho Aapo, Sulkanen Mika, Korhonen Heidi, Virta Pasi
Publisher: AMER CHEMICAL SOC
Publication year: 2020
Journal: Organic Letters
Journal name in source: ORGANIC LETTERS
Journal acronym: ORG LETT
Volume: 22
Issue: 17
First page : 6714
Last page: 6718
Number of pages: 5
ISSN: 1523-7060
eISSN: 1523-7052
DOI: https://doi.org/10.1021/acs.orglett.0c01815
Self-archived copy’s web address: https://research.utu.fi/converis/portal/detail/Publication/50235022
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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