Literature DB >> 20087996

Nucleic acids with a six-membered 'carbohydrate' mimic in the backbone.

Piet Herdewijn1.   

Abstract

Starting from pyranose nucleic acids, several series of modified nucleic acids with a six-membered carbohydrate moiety (mimic) have been synthesized and analyzed over a period of 20 years, and this work is summarized here. The process starts with structural and conformational considerations, followed by synthetic efforts and a structural analysis, and ends up with a biological confirmation of the concept, demonstrating that these modified nucleic acids represent very valuable tools in chemistry and biology.

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Year:  2010        PMID: 20087996     DOI: 10.1002/cbdv.200900185

Source DB:  PubMed          Journal:  Chem Biodivers        ISSN: 1612-1872            Impact factor:   2.408


  15 in total

1.  The conformationally constrained N-methanocarba-dT analogue adopts an unexpected C4'-exo sugar pucker in the structure of a DNA hairpin.

Authors:  Pradeep S Pallan; Victor E Marquez; Martin Egli
Journal:  Biochemistry       Date:  2012-03-20       Impact factor: 3.162

2.  Highly stable hexitol based XNA aptamers targeting the vascular endothelial growth factor.

Authors:  Elena Eremeeva; Antonios Fikatas; Lia Margamuljana; Mikhail Abramov; Dominique Schols; Elisabetta Groaz; Piet Herdewijn
Journal:  Nucleic Acids Res       Date:  2019-06-04       Impact factor: 16.971

3.  Synthesis and antisense properties of fluoro cyclohexenyl nucleic acid (F-CeNA), a nuclease stable mimic of 2'-fluoro RNA.

Authors:  Punit P Seth; Jinghua Yu; Ali Jazayeri; Pradeep S Pallan; Charles R Allerson; Michael E Østergaard; Fengwu Liu; Piet Herdewijn; Martin Egli; Eric E Swayze
Journal:  J Org Chem       Date:  2012-05-18       Impact factor: 4.354

4.  Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3'-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides.

Authors:  Martin Egli; Pradeep S Pallan; Charles R Allerson; Thazha P Prakash; Andres Berdeja; Jinghua Yu; Sam Lee; Andrew Watt; Hans Gaus; Balkrishen Bhat; Eric E Swayze; Punit P Seth
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

5.  Hybridization potential of oligonucleotides comprising 3'-O-methylated altritol nucleosides.

Authors:  G Chatelain; G Schepers; J Rozenski; Arthur Van Aerschot
Journal:  Mol Divers       Date:  2012-10-09       Impact factor: 2.943

6.  Insights from crystal structures into the opposite effects on RNA affinity caused by the S- and R-6'-methyl backbone modifications of 3'-fluoro hexitol nucleic acid.

Authors:  Pradeep S Pallan; Jinghua Yu; Charles R Allerson; Eric E Swayze; Punit Seth; Martin Egli
Journal:  Biochemistry       Date:  2011-12-29       Impact factor: 3.162

Review 7.  Artificial DNA and surface plasmon resonance.

Authors:  Roberta D'Agata; Giuseppe Spoto
Journal:  Artif DNA PNA XNA       Date:  2012-04-01

8.  TricycloDNA-modified oligo-2'-deoxyribonucleotides reduce scavenger receptor B1 mRNA in hepatic and extra-hepatic tissues--a comparative study of oligonucleotide length, design and chemistry.

Authors:  Sue Murray; Damian Ittig; Erich Koller; Andres Berdeja; Alfred Chappell; Thazha P Prakash; Michaela Norrbom; Eric E Swayze; Christian J Leumann; Punit P Seth
Journal:  Nucleic Acids Res       Date:  2012-03-30       Impact factor: 16.971

9.  C5-alkynyl-functionalized α-L-LNA: synthesis, thermal denaturation experiments and enzymatic stability.

Authors:  Pawan Kumar; Bharat Baral; Brooke A Anderson; Dale C Guenther; Michael E Østergaard; Pawan K Sharma; Patrick J Hrdlicka
Journal:  J Org Chem       Date:  2014-05-13       Impact factor: 4.354

10.  Isoguanine and 5-methyl-isocytosine bases, in vitro and in vivo.

Authors:  Omprakash Bande; Rania Abu El Asrar; Darren Braddick; Shrinivas Dumbre; Valérie Pezo; Guy Schepers; Vitor B Pinheiro; Eveline Lescrinier; Philipp Holliger; Philippe Marlière; Piet Herdewijn
Journal:  Chemistry       Date:  2015-02-13       Impact factor: 5.236

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