REACTION OF N³-BENZOYL-3′,5′-O-(DI-TERT-BUTYLSILANEDIYL)URIDINE WITH HINDERED ELECTROPHILES: INTERMOLECULAR N³ To 2′-O PROTECTING GROUP TRANSFER

REFERENCES

• Uhlman , E. and Peyman , A. 1990 . Antisense Oligonucleotides: A New Therapeutic Principle . Chem. Rev. , 90 : 543
   Web of Science ®Google Scholar
• Stein , C.A. , Subasinghe , C. , Shinozuka , K. and Cohen , J.S. 1988 . Physicochemical Properties of Phosphorothioate Oligodeoxynucleotides . Nucl. Acids Res. , 16 : 3209
   PubMed Web of Science ®Google Scholar
• Barawkar , D.A. , Kwok , Y. , Bruice , T.W. and Bruice , T.C. 2000 . Deoxynucleic Guanidine/Peptide Nucleic Acid Chimeras: Synthesis, Binding and Invasion Studies with DNA . J. Am. Chem. Soc. , 122 : 5244
   Web of Science ®Google Scholar
• Barawkar , D.A. and Bruice , T.C. 1999 . Deoxynucleic Guanidines/PNA (DNG/PNA) Chimeras: Oligonucleoside Analogue Containing Cationic Guanidinium and Neutral Amide Linkages . J. Am. Chem. Soc. , 121 : 10418
   Web of Science ®Google Scholar
• Kojima , N. and Bruice , T.C. 2000 . Replacement of the Phosphorodiester Linkages of RNA with Guanidinium Linkages: The Solid-Phase Synthesis of Ribonucleic Guanidine . Org. Lett. , 2 : 81
   PubMed Web of Science ®Google Scholar
• Ross , J. 1988 . Messenger RNA Turnover in Eukaryotic Cells . Mol. Biol. Med. , 5 : 1
   PubMedGoogle 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 . Nucl. Acids Res. , 25 : 4429
   PubMed Web of Science ®Google Scholar
• Keller , T.H. and Haner , R. 1993 . A General Method for the Synthesis of 2′-O-Modified Ribonucleosides . Helv. Chim. Acta , 76 : 884
   Web of Science ®Google Scholar
• Seeman , N.C. 1998 . DNA NANOTECHNOLOGY: Novel DNA Constructions . Annual Review of Biophysics and Biomolecular Structure , 27 : 225
   PubMedGoogle Scholar
• Seeman , N.C. 1999 . Synthetic DNA Topology Edited by: Sauvage , J.-P. and Dietrich-Buchecker , C. 323 – 356 . Weinheim : Wiley-VCH .
   Google Scholar
• Seeman , N.C. 1999 . DNA Engineering and Its Application to Nanotechnology . Trends in Biotechnology , 17 : 437
   PubMed Web of Science ®Google Scholar
• Welch , C.J. , Bazin , H. , Heikkila , J. and Chattopadhyaya , J. 1985 . Synthesis of C-5 and N-3 Arenesulfenyl Uridines. Preparation and Properties of a New Class of Uracil Protecting Group . Acta Chem. Scand. Ser. B , 39 : 203
   Google Scholar
• Akiyama , T. , Nishimoto , H. and Ozaki , S. 1990 . The Selective Protection of Uridine with a p-Methoxybenzyl Chloride: a Synthesis of 2′-O-Methyluridine . Bull. Chem. Soc. Jpn. , 63 : 3356
   Web of Science ®Google Scholar
• Robins , M.J. , Doboszewski , B. , Nillson , B.L. and Peterson , M.A. 2000 . Nucleic Acid Related Compounds. 112. Synthesis of Amide-Linked [(3′)CH2CO-NH(5′)] Nucleoside Analogs of Small Oligonucleotides . Nucleosides, Nucleotides & Nucleic Acids , 19 : 69
   PubMed Web of Science ®Google Scholar
• Lewis , A.F. , Revankar , G.R. and Hogan , M.E. 1993 . 2′-O,5-Dimethyluridine: A Total Synthesis and Single Crystal X-ray Diffraction Study . J. Heterocyclic Chem. , 30 : 1309
   Web of Science ®Google Scholar
• Sproat , B.S. , Beijer , B. and Iribarren , A. 1990 . New Synthetic Routes to Protected Purine 2′-O-Methylriboside-3′-O-Phosphoramidites Using a Novel Alkylation Procedure . Nucl. Acids Res. , 18 : 41
   PubMed Web of Science ®Google Scholar
• Asanuma , H. , Yoshida , T. , Ito , T. and Komiyama , M. 1999 . Photo-responsive Oligonucleotides Carrying Azobenzene at the 2′-Position of Uridine . Tetrahedron Lett. , 40 : 7995
   Web of Science ®Google Scholar
• Yamana , K. , Zako , H. , Asazuma , K. , Iwase , R. , Nakano , H. and Murakami , A. 2001 . Fluorescence Detection of Specific RNA Sequences Using 2′-Pyrene-Modified Oligoribonucleotides . Angew. Chem. Int. Ed. , 40 : 1104
   PubMed Web of Science ®Google Scholar
• Grotli , M. , Douglas , M. , Eritja , R. and Sproat , B.S. 1998 . 2′-O-Propargyl Oligoribonucleotides: Synthesis and Hybridisation . Tetrahedron , 54 : 5899
   Web of Science ®Google Scholar
• Grotli , M. , Beijer , B. and Sproat , B. 1999 . 2′-O-(Carbamoylmethyl)oligoribonucleotides . Tetrahedron , 55 : 4299
   Web of Science ®Google Scholar
• Wada , T. , Tobe , M. , Nagayama , T. , Furusawa , K. and Sekine , M. 1995 . Regioselective Protection of the 2′-Hydroxyl Group of N-Acyl-3′,5′-O-di(t-butyl)silanediylnucleoside Derivatives by Use of t-BuMgCl and 2-(Trimethylsilyl)ethoxymethyl Chloride . Tetrahedron Lett. , 36 : 1683
   Web of Science ®Google Scholar
• Sekine , M. , Seio , K. , Wada , T. , Sakamoto , K. and Yokoyama , S. 1994 . Chemical Synthesis and Properties of an Interresidually Cyclized Uridylyl(3′-5′)uridine as a Model of tRNA U-Turn Structure Having a Sharp . Bend. J. Am. Chem. Soc. , 116 : 4469
   Google Scholar
• Martin , P. 1995 . Ein neuer Zugang zu 2′-O-Alkylribonucleosiden und Eigenschaften deren Oligonucleotide . Helv. Chim. Acta , 78 : 486
   Web of Science ®Google Scholar
• Cuenoud , B. , Casset , F. , Huesken , D. , Natt , F. and Wolf , R.M. 1998 . Dual Recognition of Double-Stranded DNA by 2′-Aminoethoxy-Modified Oligonucleotides . Angew. Chem. Int. Ed. , 37 : 1288
   PubMed Web of Science ®Google Scholar
• Manoharan , M. , Prakash , T.P. , Barber-Peoc'h , I. , Bhat , B. , Vasquez , G. , Ross , B.S. and Cook , P.D. 1999 . N-(2-Cyanoethoxycarbonyloxy)succinimide: A New Reagent for Protection of Amino Groups in Oligonucleotides . J. Org. Chem. , 64 : 6468
   Web of Science ®Google Scholar
• Prakash , T.P. , Manoharan , M. , Kawasaki , A.M. , Lesnik , E.A. , Owens , S.R. and Vasquez , G. 2000 . 2′-O-{2-[N,N-(Dialkyl)aminooxy]ethyl}-Modified Antisense Oligonucleotides . Org. Lett. , 2 : 3995
   PubMed Web of Science ®Google Scholar
• Welch , C.J. and Chattopadhyaya , J. 1983 . 3-N-Acyl Uridines: Preparation and Properties of a New Class of Uracil Protecting Group . Acta Chem. Scand. Ser. B , 37 : 147
   Google Scholar
• Sekine , M. 1989 . General Method for the Preparation of N3- and O4-Substituted Uridine Derivatives by Phase-Transfer Reactions . J. Org. Chem. , 54 : 2321
   Web of Science ®Google Scholar
• McCloskey , J.A. 1991 . Structural Characterization of Natural Nucleosides by Mass Spectrometry . Acc. Chem. Res. , 24 : 81
   Web of Science ®Google Scholar
• Tang , X.-Q. , Liao , X. and Piccirilli , J.A. 1999 . 2′-C-Branched Ribonucleosides: Synthesis of the Phosphoramidite Derivatives of 2′-C-β-Methylcytidine and Their Incorporation into Oligonucleotides . J. Org. Chem. , 64 : 747
   PubMed Web of Science ®Google Scholar
• Sakairi , N. , Rahman , D. , Tamaki , K. and Ishido , Y. 1982 . Partial Protection of Carbohydrate Derivatives. Part 9. Equilibration between 2′,5′- and 3′,5′-di-O-Benzoyladenosine Derivatives Substituted at the N6-Position, on Silica Gel . Nucleosides & Nucleotides , 1 : 99
   Web of Science ®Google Scholar
• Velikyan , I. , Acharya , S. , Trifonova , A. , Foldesi , A. and Chattopadhyaya , J. 2001 . The pKa's of 2′-Hydroxyl Group in Nucleosides and Nucleotides . J. Am. Chem. Soc. , 123 : 2893
   PubMed Web of Science ®Google Scholar
• Grotli , M. , Douglas , M. , Beijer , B. , Garcia , R.G. , Eritja , R. and Sproat , B. 1997 . Protection of the Guanine Residue during Synthesis of 2′-O-Alkyl-guanosine Derivatives . J. Chem. Soc., Perkin Trans. 1 , : 2779
   Google Scholar