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MULTIPLE ORTHOGONAL LABELLING OF OLGONUCLEOTIDES
DEUTSCHES KREBSFORSCHUNGSZENTRUM, RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG.
DEUTSCHES KREBSFORSCHUNGSZENTRUM, RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry. DEUTSCHES KREBSFORSCHUNGSZENTRUM, RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG.
DEUTSCHES KREBSFORSCHUNGSZENTRUM, RUPRECHT-KARLS-UNIVERSITAT HEIDELBERG.
2016 (English)Patent (Other (popular science, discussion, etc.))
Abstract [en]

In Summary, the present invention concerns a method for multiple orthogonal labelling of oligonucleotides, preferably RNA or DNA, by simultaneously performing the inverse Diels-Alder reaction (DAinv) and the copper-catalyzed click reaction (CuAAC), wherein the method is employed in a single step by just adding the different reaction components together and incubating the aqueous reaction mixture prefer ably for one hour at room temperature. In detail, the reaction components are one or more N-modified labels, a copper compound, a stabilizing ligand, a reducing agent and one or more electron-deficient label-modified dienes that are added together with an at least double-modified oligonucleotide having one more nucleotides containing one or more N3-re active groups and one or more electron-rich dienophiles, wherein a terminal alkyne moiety is preferably used as N3-re active group(s) and afrans-cyclooctene moiety or norbornene is preferably used as electron-rich dienophile(s), more pref erably frans-cyclooctene. Therefore, the present invention provides a one-pot method for post-synthetic multiple orthogonal labeling of oligonucleotides, which allows the site-specific introduction of more than one label, preferably of at least two labels into oligonucleotides after solid-phase synthesis, wherein the DAinv takes place on the dienophile modification only and the CuAAC selectively takes place on the N3-reactive group modification.

Place, publisher, year, edition, pages
2016.
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:uu:diva-373487OAI: oai:DiVA.org:uu-373487DiVA, id: diva2:1278637
Patent
US US 9,315,537 B2 (2016-04-19)Available from: 2019-01-14 Created: 2019-01-14 Last updated: 2019-05-27Bibliographically approved

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Samanta, Ayan

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