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Synthesis and structural studies of S-type/N-type-locked/frozen nucleoside analogues and their incorporation in RNA-selective, nuclease resistant 2′–5′ linked oligonucleotides†
Namrata Erande,Anita D. Gunjal,Moneesha Fernandes,Rajesh Gonnade,Vaijayanti A. Kumar
Organic & Biomolecular Chemistry Pub Date : 11/07/2012 00:00:00 , DOI:10.1039/C2OB26762D
Abstract

2′-endo locked or frozen (S-type)/3′-endo locked or frozen (N-type) nucleoside analogues were synthesized. Conformational analysis based on 3JHH and NOE measurements is presented which is further confirmed by X-ray crystal structural studies. 2′–5′ isoDNA oligonucleotides (ON) were synthesized using these modified nucleoside analogues and UV-Tm studies of the resultant 2′–5′ isoDNA : RNA duplexes reflect the site- and sequence-dependent effects and confirm that the S-type sugar conformations were preferred over the N-type sugar geometry in such duplexes.

Graphical abstract: Synthesis and structural studies of S-type/N-type-locked/frozen nucleoside analogues and their incorporation in RNA-selective, nuclease resistant 2′–5′ linked oligonucleotides
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