Synthesis of Oligoribonucleotides Containing 2′-O-Methoxymethyl Group by the Phosphotriester Method

REFERENCES

• Kawasaki , A. M. , Casper , M. D. , Freier , S. M. , Lesnik , E. A. , Zounes , M. C. , Cummins , L. L. , Gonzalez , C. and Cook , P. D. 1993 . Uniformly modified 2′-deoxy-2′-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets . J. Med. Chem , 36 : 831 – 841 .
   PubMed Web of Science ®Google Scholar
• Sproat , B. S. , Lamond , A. I. , Beijer , B. , Neuner , P. and Ryder , U. 1989 . Highly efficient chemical synthesis of 2′-O-methyloligoribonucleotides and tetrabiotinylated derivatives; novel probes that are resistant to degradation by RNA or DNA specific nucleases . Nucleic Acids Res. , 17 : 3373 – 3386 .
   PubMed Web of Science ®Google Scholar
• Lamond , A. I. and Sproat , B. S. 1993 . Antisense oligonucleotides made of 2′-O-alkylRNA: Their properties and applications in RNA biochemistry . FEBS Lett. , 325 : 123 – 127 .
   PubMed Web of Science ®Google Scholar
• Altmann , K.-H. , Martin , P. , Dean , N. M. and Monia , B. P. 1997 . Second generation antisense oligonucleotides—inhibition of PKC-α and c-raf kinase expression by chimeric oligonucleotides incorporating 6′-substituted carbocyclic nucleosides and 2′-O-ethylene glycol substituted ribonucleosides . Nucleosides & Nucleotides , 16 : 917 – 926 .
   Google Scholar
• Saneyoshi , H. , Seio , K. and Sekine , M. 2005 . A general method for the synthesis of 2′-O-cyanoethylated oligoribonucleotides having promising hybridization affinity for DNA and RNA and enhanced nuclease resistance . J. Org. Chem , 70 : 10453 – 10460 .
   PubMed Web of Science ®Google Scholar
• Efimov , V. , Buryakova , A. , Dubey , I. , Polushin , N. , Chakhmakhcheva , O. and Ovchinnikov , Yu . 1986 . Application of new catalytic phosphate protecting groups for the highly efficient phosphotriester oligonucleotide synthesis . Nucleic Acids Res. , 14 : 6526 – 6540 .
   Web of Science ®Google Scholar
• Polushin , N. , Smirnov , I. , Verentchikov , A. and Coull , J. 1996 . Synthesis of oligonucleotides containing 2′-azido- and 2′-amino-2′-deoxyuridine using phosphotriester chemistry . Tetrahedrom Lett. , 37 : 3227 – 3230 .
   Web of Science ®Google Scholar
• Almer , H. , Szabo , T. and Stawinski , J. 2004 . A new approach to stereospecific synthesis of P-chiral phosphorothioates. Preparation of diastereomeric dithymidyl-(3′-5′) phosphorothioates . Chem. Commun. , : 290 – 291 .
   PubMed Web of Science ®Google Scholar
• Efimov , V. A. , Molchanova , N. S. and Chakhmakhcheva , O. G. 2007 . Approach to the synthesis of natural and modified oligonucleotides by the phosphotriester method using o-nucleophilic intramolecular catalysis . Nucleosides Nucleotides Nucleic Acids , 26 : 1087 – 1093 .
   PubMed Web of Science ®Google Scholar
• Efimov , V. A. , Aralov , A. V. , Fedunin , S. V. , Klykov , V. N. and Chakhmakhcheva , O. G. 2009 . An azidomethyl protective group in the synthesis of oligoribonucleotides by the phosphotriester method . Russ. J. Bioorg. Chem. , 35 : 250 – 253 .
   Web of Science ®Google Scholar
• Efimov , V. A. , Aralov , A. V. , Klykov , V. N. and Chakhmakhcheva , O. G. 2009 . Synthesis of RNA by the rapid phosphotriester method using azido-based 2′-O-protecting groups . Nucleosides Nucleotides Nucleic Acids , 28 : 846 – 865 .
   PubMed Web of Science ®Google Scholar
• Efimov , V. A. , Aralov , A. V. , Grachev , S. A. and Chakhmakhcheva , O. G. 2010 . N-azidomethylbenzoyl blocking group in the phosphotriester synthesis of oligoribonucleotides . Russ. J. Bioorg. Chem. , 36 : 628 – 633 .
   Web of Science ®Google Scholar
• Efimov , V. A. , Aralov , A. V. and Chakhmakhcheva , O. G. 2011 . Methoxymethyl and (p-nitrobenzyloxy)methyl groups in synthesis of oligoribunucleotides by the phosphotriester method . Russ. J. Bioorg. Chem. , 37 : 254 – 258 .
   Web of Science ®Google Scholar
• Aralov , A. V. , Klykov , V. N. , Chakhmakhcheva , O. G. and Efimov , V. A. 2011 . Monomers containing 2′-O-alkoxymethyl groups as synthons for the oligonucleotide synthesis by the phosphotriester method . Russ. J. Bioorg. Chem , 37 : 586 – 592 .
   Web of Science ®Google Scholar
• Greene , T. W. and Wuts , P. G.M. 1999 . Protective Groups in Organic Synthesis , 4th ed. , 27 – 33 . New York : Wiley .
   Google Scholar
• Groziak , M. P. and Koohang , A. 1992 . Facile addition of hydroxylic nucleophiles to the formyl group of uridine-6-carboxaldehydes . J. Org. Chem. , 57 : 940 – 944 .
   Web of Science ®Google Scholar
• Tanaka , H. , Hayakawa , H. and Miyasaka , T. 1981 . Synthesis of 6-aroyluridine from uridine via regiospecific lithiatio . Chem. Pharm. Bull. , 29 : 3565 – 3572 .
   Web of Science ®Google Scholar
• Nishino , S. and Ishido , Y. 1986 . Partial protection of carbohydrate derivatives. Part 22. Further improvement in introduction of methoxymethyl group to hydroxyl groups of carbohydrate derivatives . J. Carbohydr. Chem. , 5 : 313 – 327 .
   Web of Science ®Google Scholar
• Bizdena , E. , Rozners , E. and Stromberg , R. 1996 . Synthesis and properties of 2′-O-methoxymethyl oligonucleotides . Collect. Czech. Chem. Commun. , : s283 – s286 .
   Google Scholar
• Talbot , D. C. , Davies , J. , Callies , S. , Andre , V. , Lahn , M. , Ang , J. , De Bono , J. S. and Ranson , M. 2008 . First human dose study evaluating safety and pharmacokinetics of LY2181308, an antisense oligonucleotide designed to inhibit survivin . J. Clin. Oncol. (Meeting Abstracts) , 26 : 3518
   Web of Science ®Google Scholar
• Pennati , M. , Folini , M. and Zaffaroni , N. 2010 . “ Targeting survivin in cancer therapy: Pre-clinical studies ” . In Apoptosome , Edited by: Cecconi , F. and D'Amelio , M. 147 – 168 . Dordrecht : Springer .
   Google Scholar
• Shiba , Y. , Masuda , H. , Watanabe , N. , Ego , T. , Takagaki , K. , Ishiyama , K. , Ohgi , T. and Yano , J. 2007 . Chemical synthesis of a very long oligoribonucleotide with 2-cyanoethoxymethyl (CEM) as the 2′-O-protecting group: Structural identification and biological activity of a synthetic 110mer precursor-microRNA candidate . Nucleic Acids Res , 35 : 3287 – 3296 .
   PubMed Web of Science ®Google Scholar
• Han , J. H. , Kwon , Y. E. , Sohn , J.-H. and Ryu , D. H. 2010 . A facile method for the rapid and selective deprotection of methoxymethyl (MOM) ethers . Tetrahedron , 66 : 1673 – 1677 .
   Web of Science ®Google Scholar
• Eskandari , R. , Jayakanthan , K. , Kuntz , D. A. , Rose , D. R. and Pinto , B. M. 2010 . Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor . Bioorg. Med. Chem. , 18 : 2829 – 2835 .
   PubMed Web of Science ®Google Scholar
• Pechenov , A. E. , Zavgorodny , S. G. , Shvets , V. L. and Miroshnikov , A. I. 2000 . The S, X-acetals in nucleoside chemistry. I. The synthesis of 2′- and 5′-O-methylthiomethylribonucleosides . Russ. J. Bioorg. Chem. , 26 : 327 – 333 .
   Google Scholar