Literature DB >> 23193103

Synthesis, duplex stabilization and structural properties of a fluorinated carbocyclic LNA analogue.

Punit P Seth1, Pradeep S Pallan, Eric E Swayze, Martin Egli.   

Abstract

DNA oligonucleotides modified with nucleoside monomers which have an electron withdrawing group (EWG) at the 2'-position of the furanose ring form more stable duplexes with complementary RNA as compared to unmodified DNA. Here we show that an anti-periplanar orientation of the nucleobase and the 2'-EWG is important for optimal duplex stabilization even for nucleic acid analogues with conformationally locked furanose rings.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 23193103      PMCID: PMC3684079          DOI: 10.1002/cbic.201200669

Source DB:  PubMed          Journal:  Chembiochem        ISSN: 1439-4227            Impact factor:   3.164


  21 in total

1.  The many roles for fluorine in medicinal chemistry.

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Journal:  J Med Chem       Date:  2008-06-21       Impact factor: 7.446

2.  RNA hydration: a detailed look.

Authors:  M Egli; S Portmann; N Usman
Journal:  Biochemistry       Date:  1996-07-02       Impact factor: 3.162

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Authors:  Amritraj Patra; Michael Paolillo; Klaus Charisse; Muthiah Manoharan; Eriks Rozners; Martin Egli
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4.  A new class of SN2 reactions catalyzed by protic solvents: Facile fluorination for isotopic labeling of diagnostic molecules.

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Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

5.  Synthesis and biophysical evaluation of 2',4'-constrained 2'O-methoxyethyl and 2',4'-constrained 2'O-ethyl nucleic acid analogues.

Authors:  Punit P Seth; Guillermo Vasquez; Charles A Allerson; Andres Berdeja; Hans Gaus; Garth A Kinberger; Thazha P Prakash; Michael T Migawa; Balkrishen Bhat; Eric E Swayze
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

6.  Conformational influence of the ribose 2'-hydroxyl group: crystal structures of DNA-RNA chimeric duplexes.

Authors:  M Egli; N Usman; A Rich
Journal:  Biochemistry       Date:  1993-04-06       Impact factor: 3.162

7.  Convenient synthesis of fluorinated nucleosides with perfluoroalkanesulfonyl fluorides.

Authors:  Satoshi Takamatsu; Satoshi Katayama; Naoko Hirose; Etienne De Cock; Geert Schelkens; Marc Demillequand; Jozef Brepoels; Kunisuke Izawa
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2002 Nov-Dec       Impact factor: 1.381

8.  Synthesis of functionalized carbocyclic locked nucleic acid analogues by ring-closing diene and enyne metathesis and their influence on nucleic acid stability and structure.

Authors:  Surender Kumar; Marianne H Hansen; Nanna Albaek; Signe I Steffansen; Michael Petersen; Poul Nielsen
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

9.  Differential stability of 2'F-ANA*RNA and ANA*RNA hybrid duplexes: roles of structure, pseudohydrogen bonding, hydration, ion uptake and flexibility.

Authors:  Jonathan K Watts; Nerea Martín-Pintado; Irene Gómez-Pinto; Jeremy Schwartzentruber; Guillem Portella; Modesto Orozco; Carlos González; Masad J Damha
Journal:  Nucleic Acids Res       Date:  2010-01-13       Impact factor: 16.971

10.  Potent inhibition of microRNA in vivo without degradation.

Authors:  Scott Davis; Stephanie Propp; Susan M Freier; Laura E Jones; Martin J Serra; Garth Kinberger; Balkrishen Bhat; Eric E Swayze; C Frank Bennett; Christine Esau
Journal:  Nucleic Acids Res       Date:  2008-11-16       Impact factor: 16.971

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