Synthesis and Excellent Duplex Stability of Oligonucleotides Containing 2'-Amino-LNA Functionalized with Galactose Units

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Rajesh KumarJesper Wengel

Abstract

A convenient method for the preparation of oligonucleotides containing internally-attached galactose and triantennary galactose units has been developed based on click chemistry between 2'-N-alkyne 2'-amino-LNA nucleosides and azido-functionalized galactosyl building blocks. The synthesized oligonucleotides show excellent binding affinity and selectivity towards complementary DNA/RNA strands with an increase in the melting temperature of up to +23.5 °C for triply-modified variants.

References

Jan 1, 1982·Annual Review of Biochemistry·G Ashwell, J Harford
Apr 17, 2001·The Journal of Organic Chemistry·A Patel, T K Lindhorst
Oct 11, 2001·Journal of the American Chemical Society·G A MeintsG P Drobny
Feb 12, 2002·Bioorganic & Medicinal Chemistry·Christian J Leumann
Nov 20, 2002·Accounts of Chemical Research·Eric T Kool
Jun 11, 2004·Annual Review of Biochemistry·Aziz SancarStuart Linn
Sep 8, 2004·Current Opinion in Pharmacology·Simon W JonesMark A Lindsay
May 17, 2006·Clinical and Experimental Pharmacology & Physiology·Jasmine H P ChanW S Fred Wong
Oct 20, 2006·Current Opinion in Chemical Biology·Charles Wilson, Anthony D Keefe
Nov 15, 2006·Organic & Biomolecular Chemistry·James N Wilson, Eric T Kool
Feb 1, 2007·Chemical Society Reviews·Jonathan L SesslerJanarthanan Jayawickramarajah
Jul 14, 2007·BioDrugs : Clinical Immunotherapeutics, Biopharmaceuticals and Gene Therapy·Arnold Grünweller, Roland K Hartmann
Feb 26, 2008·Seminars in Cancer Biology·Jan StenvangSakari Kauppinen
Mar 25, 2008·Bioorganic & Medicinal Chemistry·Oleg KhorevBeat Ernst
Apr 3, 2008·Angewandte Chemie·Philipp M E GramlichThomas Carell
Aug 5, 2008·The Journal of Organic Chemistry·Gerald Enderlin, Poul Nielsen
Nov 15, 2008·Chemical Communications : Chem Comm·Samuel H Weisbrod, Andreas Marx
Sep 10, 2009·Chembiochem : a European Journal of Chemical Biology·Neil M Bell, Jason Micklefield
Oct 30, 2009·Bioorganic & Medicinal Chemistry Letters·Frank J HernandezBirte Vester
Mar 18, 2010·Chemical Communications : Chem Comm·Raghavendra KikkeriPeter H Seeberger
Mar 24, 2010·Chemical Society Reviews·Afaf H El-Sagheer, Tom Brown
Apr 23, 2010·Chemical Society Reviews·Arnold J BoersmaGerard Roelfes
Sep 9, 2010·Bioorganicheskaia khimiia·A V UstinovV A Korshun
Mar 25, 2011·Biochemical Society Transactions·Keith R Fox, Tom Brown
Mar 31, 2011·Future Medicinal Chemistry·Tsuyoshi YamamotoSatoshi Obika
Jul 2, 2011·International Journal of Nanomedicine·Yan GaoXiao-Rong Li
Sep 17, 2011·Chemistry & Biodiversity·Thazha P Prakash
Nov 10, 2011·Chemical Communications : Chem Comm·Lukas M ArtnerChristian P R Hackenberger
Aug 28, 2012·Chemistry & Biology·Glen F Deleavey, Masad J Damha
Nov 14, 2012·The Journal of Organic Chemistry·Andreas Stahl MadsenJesper Wengel
Nov 28, 2012·Nucleic Acid Therapeutics·Kasper K Karlsen, Jesper Wengel
Dec 4, 2012·Chemical Communications : Chem Comm·I Kira AstakhovaJesper Wengel
Dec 21, 2012·Chemical Society Reviews·Nicolas SpinelliFrançois Morvan
May 18, 2013·Organic & Biomolecular Chemistry·I Kira AstakhovaJesper Wengel
Oct 11, 2013·Chemical Communications : Chem Comm·Anna S JørgensenI Kira Astakhova
Apr 23, 2014·Accounts of Chemical Research·I Kira Astakhova, Jesper Wengel
Dec 2, 2014·Journal of the American Chemical Society·Jayaprakash K NairMuthiah Manoharan

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Citations

Oct 14, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Harri Lönnberg
Jan 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shoko YamashitaYoshiyuki Hari
Aug 30, 2019··Vishnudatt PandeyRajendra Prasad Ojha

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Methods Mentioned

BETA
antisense oligonucleotides
column chromatography

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