Efficient access to 3'-terminal azide-modified RNA for inverse click-labeling patterns

Bioconjugate Chemistry
Tobias SantnerRonald Micura

Abstract

Labeled RNA becomes increasingly important for molecular diagnostics and biophysical studies on RNA with its diverse interaction partners, which range from small metabolites to large macromolecular assemblies, such as the ribosome. Here, we introduce a fast synthesis path to 3'-terminal 2'-O-(2-azidoethyl) modified oligoribonucleotides for subsequent bioconjugation, as exemplified by fluorescent labeling via Click chemistry for an siRNA targeting the brain acid-soluble protein 1 gene (BASP1). Importantly, the functional group pattern is inverse to commonly encountered alkyne-functionalized "click"-able RNA and offers increased flexibility with respect to multiple and stepwise labeling of the same RNA molecule. Additionally, our route opens up a minimal step synthesis of 2'-O-(2-aminoethyl) modified pyrimidine nucleoside phosphoramidites which are of widespread use to generate amino-modified RNA for N-hydroxysuccinimide (NHS) ester-based conjugations.

References

Jan 26, 1996·The Journal of Organic Chemistry·Danny P. C. McGeeYansheng Zhai
May 22, 2003·Bioconjugate Chemistry·Charles C-Y WangJingyue Ju
Dec 7, 2007·The Journal of Organic Chemistry·Anup M JawalekarFloris L van Delft
Jun 5, 2008·The Journal of Organic Chemistry·Romualdas Smicius, Joachim W Engels
Jul 11, 2008·Drug Discovery Today·Jonathan K WattsMasad J Damha
Aug 30, 2008·Nature·Yanli WangDinshaw J Patel
Sep 25, 2008·Angewandte Chemie·Philipp M E GramlichThomas Carell
Nov 15, 2008·Chemical Communications : Chem Comm·Samuel H Weisbrod, Andreas Marx
Mar 20, 2009·Proceedings of the National Academy of Sciences of the United States of America·Markus HartlKlaus Bister
Apr 22, 2009·Chembiochem : a European Journal of Chemical Biology·Ulrike RiederRonald Micura
Aug 12, 2009·The Journal of Organic Chemistry·Gwladys PourceauFrançois Morvan
Aug 29, 2009·Angewandte Chemie·Ellen M Sletten, Carolyn R Bertozzi
Feb 6, 2010·Chembiochem : a European Journal of Chemical Biology·Falk Wachowius, Claudia Höbartner
Feb 10, 2010·Proceedings of the National Academy of Sciences of the United States of America·Markus HartlKlaus Bister
Mar 24, 2010·Chemical Society Reviews·Afaf H El-Sagheer, Tom Brown
Mar 31, 2010·Chemical Society Reviews·John C Jewett, Carolyn R Bertozzi
Dec 7, 2010·Chembiochem : a European Journal of Chemical Biology·Eduardo Paredes, Subha R Das
Dec 21, 2010·Chembiochem : a European Journal of Chemical Biology·Michaela AignerRonald Micura
May 5, 2011·Bioconjugate Chemistry·Anu KiviniemiHarri Lönnberg
Sep 3, 2011·Angewandte Chemie·Sander S van BerkelJan C M van Hest
Dec 14, 2011·ACS Chemical Biology·Kelly PhelpsPeter A Beal
Dec 20, 2011·Nucleic Acids Research·Antonia S CardewKeith R Fox
Jun 20, 2012·Bioconjugate Chemistry·Juliane SchochAndres Jäschke
Jul 21, 2012·Journal of the American Chemical Society·Julian WillibaldThomas Carell
Aug 16, 2012·Chemical Communications : Chem Comm·Montserrat ShelbourneTom Brown
Oct 6, 2012·Chemical Communications : Chem Comm·Salifu Seidu-LarryOlwen Domingo
Dec 1, 2012·Chemistry : a European Journal·Matthieu FonvielleMélanie Ethève-Quelquejeu
Feb 27, 2013·Proceedings of the National Academy of Sciences of the United States of America·Andrea HallerRonald Micura
Apr 3, 2013·Bioorganic & Medicinal Chemistry·Sylwia SowaChristian P R Hackenberger
May 15, 2013·Bioorganic & Medicinal Chemistry·Lea BüttnerClaudia Höbartner
Aug 14, 2013·Proceedings of the National Academy of Sciences of the United States of America·Marie F SoulièreRonald Micura
Oct 12, 2013·Angewandte Chemie·Ugo PradèreJonathan Hall
May 18, 1998·Angewandte Chemie·Bernard CuenoudHeinz E Moser

❮ Previous
Next ❯

Citations

Jan 26, 2016·Bioconjugate Chemistry·Ugo Pradere, Jonathan Hall
Feb 20, 2016·Bioconjugate Chemistry·Nicole KretschyMark M Somoza
Jul 6, 2014·Journal of Pharmaceutical Sciences·Flavia LaffleurJulia Griessinger
Sep 19, 2015·Nucleic Acids Research·Anupam A SawantSeergazhi G Srivatsan
Jan 23, 2016·Chemical Reviews·Vinod K TiwariXi Chen
Aug 31, 2016·Topics in Current Chemistry·Stephanie Kath-Schorr
Feb 24, 2015·ACS Medicinal Chemistry Letters·Brandon J PeelJean-Paul Desaulniers
Aug 27, 2014·Organic Letters·Maksim A FomichVadim V Shmanai
Jul 30, 2014·Bioconjugate Chemistry·Anna Maria PykaStephanie Kath-Schorr
Mar 7, 2017·Journal of Inorganic Biochemistry·Leah M SeebaldMaksim Royzen
Apr 14, 2017·Bioconjugate Chemistry·Jerrin Thomas George, Seergazhi G Srivatsan
Feb 22, 2017·Methods : a Companion to Methods in Enzymology·Jerrin Thomas George, Seergazhi G Srivatsan
Feb 22, 2017·Chemical Communications : Chem Comm·Albert GandiosoMontserrat Terrazas
Jun 10, 2016·Organic & Biomolecular Chemistry·Antoine MaruaniVijay Chudasama
May 14, 2016·Organic & Biomolecular Chemistry·Anupam A SawantSeergazhi G Srivatsan
Dec 8, 2016·Oncotarget·Philipp RaffeinerKlaus Bister
Jul 24, 2020·International Journal of Molecular Sciences·Olga A KrashenininaAlya G Venyaminova
Sep 7, 2016·Chembiochem : a European Journal of Chemical Biology·Sarah NainarRobert C Spitale
Oct 18, 2014·Chemistry : a European Journal·André KrauseAndres Jäschke
Oct 8, 2020·Chemical Communications : Chem Comm·Jerrin Thomas George, Seergazhi G Srivatsan
Jun 25, 2021·Chemical Reviews·Anand K AgrahariVinod K Tiwari
Mar 23, 2017·Inorganic Chemistry·Leah M SeebaldMaksim Royzen
Oct 23, 2020·Bioconjugate Chemistry·Manisha B Walunj, Seergazhi G Srivatsan

❮ Previous
Next ❯

Methods Mentioned

BETA
fluorescence resonance
fluorescence microscopy
FRET
column chromatography
transfection

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chembiochem : a European Journal of Chemical Biology
Markus GrammelNicholas K Conrad
Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Subhadeep Roy, Marvin Caruthers
Current Opinion in Drug Discovery & Development
Serge L Beaucage
© 2021 Meta ULC. All rights reserved