Issue 25, 2024, Issue in Progress
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RSC Advances

Synthesis and stability studies of bicyclo[6.1.0]nonyne scaffolds for automated solid-phase oligonucleotide synthesis†

Kristina Karalė, ORCID logo *ab   Martin Bollmark,b   Antanas Karalius,b   Mónica Lopes,bc   Oswaldo Pérez,bd   Roger Strömberg ORCID logo ae  and  Ulf Tedebark ORCID logo *b  

* Corresponding authors

a Department of Biosciences and Nutrition, Karolinska Institutet, Neo, Huddinge, Sweden
E-mail: kristina.karale@ri.se

b RISE, Department Chemical Process and Pharmaceutical Development, Forskargatan 18, SE-15136 Södertälje, Sweden
E-mail: ulf.tedebark@ri.se

c School of Chemistry, University of Southampton, Southampton, UK

d Faculty of Pharmaceutical Sciences, University of Iceland, Sæmundargata 2, Reykjavík, Iceland

e Department of Laboratory Medicine, Karolinska Institutet, ANA Futura, Huddinge, Sweden

Abstract

Two novel bicyclo[6.1.0]nonyne (BCN) linker derivatives, which can be directly incorporated into oligonucleotide sequences during standard automated solid-phase synthesis, are reported. Stabilities of BCN-carbinol and two BCN-oligonucleotides are evaluated under acidic conditions. In addition, derivatized BCN linkers (non-acidic and acid treated) are evaluated for strain-promoted alkyne–azide cycloaddition (SPAAC).

Graphical abstract: Synthesis and stability studies of bicyclo[6.1.0]nonyne scaffolds for automated solid-phase oligonucleotide synthesis

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Article information

DOI
https://doi.org/10.1039/D3RA08732H
Article type
Paper
Submitted
21 Dec 2023
Accepted
09 May 2024
First published
29 May 2024
This article is Open Access
Creative Commons BY license

RSC Adv., 2024,14, 17406-17412

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Synthesis and stability studies of bicyclo[6.1.0]nonyne scaffolds for automated solid-phase oligonucleotide synthesis

K. Karalė, M. Bollmark, A. Karalius, M. Lopes, O. Pérez, R. Strömberg and U. Tedebark, RSC Adv., 2024, 14, 17406 DOI: 10.1039/D3RA08732H

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