Automated Solid‐Phase Oligo (disulfide) Synthesis
Abstract: A method for automated solid‐phase synthesis of oligo (disulfide) s was developed. It is based on a synthetic cycle comprising removal of a protecting group from a resin‐bound thiol followed by treatment with monomers containing a thiosulfonate as an activated precursor. For ease of purification and characterization, the disulfide oligomers were synthesized as extensions of oligonucleotides on an automated oligonucleotide synthesizer. Six different dithiol monomer building blocks were synthesized. Sequence‐defined oligomers of up to seven disulfide units were synthesized and purified. The sequence of the oligomer was confirmed by tandem MS/MS analysis. One of the monomers contains a coumarin cargo that can be released by a thiol‐mediated release mechanism. When the monomer was incorporated into an oligo (disulfide) and subjected to reducing conditions, the cargo was released under near‐physiological conditions, which underlines the potential use of these molecules in drug delivery systems.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Automated Solid‐Phase Oligo (disulfide) Synthesis ; day:27 ; month:04 ; year:2023 ; extent:10
Angewandte Chemie ; (27.04.2023) (gesamt 10)
- Creator
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Frandsen, Martin
El‐Chami, Kassem
Palmfeldt, Johan
Melgaard Smidt, Jakob
Langballe, Maja E. T.
Sandahl, Alexander
Gothelf, Kurt V.
- DOI
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10.1002/ange.202303170
- URN
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urn:nbn:de:101:1-2023042815084009676425
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:51 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Frandsen, Martin
- El‐Chami, Kassem
- Palmfeldt, Johan
- Melgaard Smidt, Jakob
- Langballe, Maja E. T.
- Sandahl, Alexander
- Gothelf, Kurt V.
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