2′-O-Hydroxyalkoxymethylribonucleosides and their Incorporation into Oligoribonucleotides

REFERENCES

• Kurrech , J. 2003 . Antisence technologies. Improvements through novel chemical modifications . Eur. J. Biochem. , 270 : 1628 – 1644 .
   PubMedGoogle Scholar
• Sioud , M. and Iversen , P. O. 2005 . Ribozymes, DNAzymes and small interfering RNAs as therapeutics . Curr. Drug Targets , 6 : 647 – 653 .
   PubMed Web of Science ®Google Scholar
• Coppelli , F. M. and Grandis , J. R. 2005 . Oligonucleotides as anticancer agents: From the benchside to the clinical and beyond . Curr. Pharm. Des. , 11 : 2825 – 2840 .
   PubMed Web of Science ®Google Scholar
• Manoharan , M. 1999 . 2′-Carbohadrate modification in antisense oligonucleotide therapy: Importance of conformation, configuration and conjugation . Biochim. Biophys. Acta , 1489 : 117 – 130 .
   PubMed Web of Science ®Google Scholar
• Freier , S. M. and Altmann , K.-H. 1997 . The ups and downs of nucleic acid duplex stability: Structure-stability studies on chemically-modified DNA:RNA duplexes . Nucleic Acids Res. , 25 : 4429 – 4443 .
   PubMed Web of Science ®Google Scholar
• Jin , S. , Miduturu , C. V. , McKinney , D. C. and Silverman , S. K. 2005 . Synthesis of amine- and thiole-modified nucleoside phosphoramidites for site-specific introduction of biophysical probes into RNA . J. Org. Chem. , 70 : 4284 – 4299 .
   PubMed Web of Science ®Google Scholar
• Zatsepin , T. S. , Romanova , E. A. and Oretskaya , T. S. 2002 . Synthesis of 2′-O-alkylnucleosides . Russ. Chem. Rev. , 71 : 513 – 534 .
   Google Scholar
• Efimtseva , E. V. and Mikhailov , S. N. 2004 . Disaccharide nucleosides . Russ. Chem. Rev. , 73 : 401 – 414 .
   Google Scholar
• Nauwelaerts , K. , Efimtseva , E. V. , Mikhailov , S. N. and Herdewijn , P. 2004 . “ Disaccharide nucleosides, an important group of natural compounds ” . In Frontiers in Nucleosides and Nucleic Acids , Edited by: Schinazi , R. F. and Liotta , D. C. 187 – 220 . Tucker, GA : IHL Press .
   Google Scholar
• Mikhailov , S. N. , Efimtseva , E. V. , Gurskaya , G. V. , Zavodnik , V. E. , De Bruyn , A. , Janssen , G. , Rozenski , J. and Herdewijn , P. 1997 . An efficient synthesis and physico-chemical properties of 2′ -O-β -D-ribofuranosyl-nucleosides, minor tRNA components . J. Carbohydr. Chem. , 16 : 75 – 92 .
   Web of Science ®Google Scholar
• Mikhailov , S. N. , Rodionov , A. A. , Efimtseva , E. V. , Ermolinsky , B. S. , Fomitcheva , M. V. , Padyukova , N. Sh. , Rothenbacher , K. , Lescrinier , E. and Herdewijn , P. 1998 . Formation of Trisaccharide Nucleoside during disaccharide nucleoside synthesis . Eur. J. Org. Chem. , : 2193 – 2199 .
   Web of Science ®Google Scholar
• Mikhailov , S. N. and Efimtseva , E. V. 2002 . Disaccharide nucleosides and oligonucleotides on their basis . Collect. Czech. Chem. Commun. Symp. Ser. , 5 : 181 – 194 .
   Google Scholar
• Bobkov , G. V. , Brilliantov , K. V. , Mikhailov , S. N. , Rozenski , J. , Van Aerschot , A. and Herdewijn , P. 2006 . Synthesis of oligoribonucleotides containing pyrimidine 2′-O-[(hydroxyalkoxy)methyl] ribonucleosides . Collection Czech. Chem. Comm. , 71 : 804 – 819 .
   Google Scholar
• Efimtseva , E. V. , Bobkov , G. V. , Mikhailov , S. N. , Van Aerschot , A. , Schepers , G. , Busson , R. , Rozenski , J. and Herdewijn , P. 2001 . Oligonucleotides containing disaccharide nucleosides . Helv. Chim. Acta , 84 : 2387 – 2397 .
   Web of Science ®Google Scholar
• Senkus , M. 1946 . Reaction of some cyclic acetals with acetic anhydride . J. Am. Chem. Soc. , 68 : 734 – 736 .
   Web of Science ®Google Scholar
• Xu , D. , Kang , H. , Fisher , M. and Juliano , R. L. 2004 . strategies for the inhibition of MDR1 gene expression . Mol. Pharmacol. , 66 : 268 – 275 .
   PubMed Web of Science ®Google Scholar