Literature DB >> 18052191

Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition.

Anup M Jawalekar1, Nico Meeuwenoord, J Sjef G O Cremers, Herman S Overkleeft, Gijs A van der Marel, Floris P J T Rutjes, Floris L van Delft.   

Abstract

A procedure is presented for copper(I)-catalyzed [3+2] cycloaddition of nucleosides and nucleotides in near-quantitative yield. Azido-alkyne cycloaddition was applied for the preparation of a range of adenosine dimers and derivatives with versatile functionality, as well as for the smooth condensation of two oligonucleotide strands. The described technology may find valuable application in the synthesis of oligonucleotide dimers and conjugates.

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Year:  2007        PMID: 18052191     DOI: 10.1021/jo702023s

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  16 in total

1.  C2'-pyrene-functionalized triazole-linked DNA: universal DNA/RNA hybridization probes.

Authors:  Sujay P Sau; Patrick J Hrdlicka
Journal:  J Org Chem       Date:  2011-11-16       Impact factor: 4.354

2.  2D IR photon echo of azido-probes for biomolecular dynamics.

Authors:  Matthew J Tucker; Xin Sonia Gai; Edward E Fenlon; Scott H Brewer; Robin M Hochstrasser
Journal:  Phys Chem Chem Phys       Date:  2010-12-02       Impact factor: 3.676

3.  Strain-promoted "click" chemistry for terminal labeling of DNA.

Authors:  Isaac S Marks; Jun Sung Kang; Brady T Jones; Kevin J Landmark; Andrew J Cleland; T Andrew Taton
Journal:  Bioconjug Chem       Date:  2011-06-02       Impact factor: 4.774

4.  Triazole-linked inhibitors of inosine monophosphate dehydrogenase from human and Mycobacterium tuberculosis.

Authors:  Liqiang Chen; Daniel J Wilson; Yanli Xu; Courtney C Aldrich; Krzysztof Felczak; Yuk Y Sham; Krzysztof W Pankiewicz
Journal:  J Med Chem       Date:  2010-06-24       Impact factor: 7.446

5.  Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.

Authors:  Jessica Zayas; Marie Annoual; Jayanta Kumar Das; Quentin Felty; Walter G Gonzalez; Jaroslava Miksovska; Nima Sharifai; Akira Chiba; Stanislaw F Wnuk
Journal:  Bioconjug Chem       Date:  2015-07-02       Impact factor: 4.774

Review 6.  Total RNA Synthesis and its Covalent Labeling Innovation.

Authors:  Hongling Zhou; Yuanyuan Li; Youfang Gan; Rui Wang
Journal:  Top Curr Chem (Cham)       Date:  2022-02-26

Review 7.  Covalent labeling of nucleic acids.

Authors:  Nils Klöcker; Florian P Weissenboeck; Andrea Rentmeister
Journal:  Chem Soc Rev       Date:  2020-10-21       Impact factor: 54.564

8.  Two-Dimensional Infrared Study of Vibrational Coupling between Azide and Nitrile Reporters in a RNA Nucleoside.

Authors:  Andrew J Schmitz; David G Hogle; Xin Sonia Gai; Edward E Fenlon; Scott H Brewer; Matthew J Tucker
Journal:  J Phys Chem B       Date:  2016-08-24       Impact factor: 2.991

9.  Site-specific terminal and internal labeling of RNA by poly(A) polymerase tailing and copper-catalyzed or copper-free strain-promoted click chemistry.

Authors:  Marie-Luise Winz; Ayan Samanta; Dirk Benzinger; Andres Jäschke
Journal:  Nucleic Acids Res       Date:  2012-02-16       Impact factor: 16.971

10.  Site-specific labeling of RNA by combining genetic alphabet expansion transcription and copper-free click chemistry.

Authors:  Tatsuhiko Someya; Ami Ando; Michiko Kimoto; Ichiro Hirao
Journal:  Nucleic Acids Res       Date:  2015-06-29       Impact factor: 16.971

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