The Spontaneous Rearrangement of 2,4-Dinitrophenyl Substituent in Ribonucleosides Under Neutral Conditions

REFERENCES

• Chen , X. L. , Shen , L. and Wang , J. H. 2004 . Poly-2′-DNP-RNAs with enhanced efficacy for inhibiting cancer cell growth . Oligonucleotides , 14 : 90 – 99 .
   PubMedGoogle Scholar
• Shen , L. , Zhang , C. J. , Ambrus , J. L. and Wang , J. H. 2005 . Silencing of human c-myc oncogene expression by poly-DNP-RNA . Oligonucleotides , 15 : 23 – 35 .
   PubMedGoogle Scholar
• Ru , K. , Schmitt , S. , James , W. I. and Wang , J. H. 1999 . Growth inhibition and antimetastatic effect of antisense poly-DNP-RNA on human breast cancer cells . Oncology Res. , 11 : 505 – 512 .
   PubMedGoogle Scholar
• Wang , A. H. and Wang , J. H. 1999 . Effective treatment of murine leukemia with antisense poly-2′-O-(2,4-dinitrophenyl)-oligoribonucleotides . Antisense & Nucleic Acid Drug Development , 9 : 43 – 51 .
   PubMedGoogle 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
• Beigelman , L. , Karpeisky , A. , Matulicadamic , J. , Haeberli , P. , Sweedler , D. and Usman , N. 1995 . Synthesis of 2′-modified nucleotides and their incorporation into hammerhead ribozymes . Nucleic Acids Res. , 23 : 4434 – 4442 .
   PubMed Web of Science ®Google Scholar
• Bhide , R. S. , Levison , B. S. , Sharma , R. B. , Ghosh , S. and Salomon , R. G. 1986 . Di-tert-butylmethylsilyl (Dtbms) trifluoromethanesulfonate—preparation and synthetic applications of Dtbms esters and enol ethers . Tetrahedron Lett. , 27 : 671 – 674 .
   Web of Science ®Google Scholar
• Horton , D. and Luetzow , A. E. 1971 . Migration of the O-p-nitrophenyl group. Mechanism whereby p-nitrophenyl alpha-D-glycosides liberate p-nitrophenoxide in alkaline solution . J. Chem. Soc. D: Chem. Comm. , : 79 – 81 .
   Google Scholar
• Klemer , A. and Kleefeldt , L. 1975 . Synthesis and properties of some D-glucose 2,4-dinitrophenyl ethers . Ann. Chem. Justus Liebig , : 1658 – 1666 .
   Google Scholar
• Nawrot , B. , Pankiewicz , K. W. , Zepf , R. A. and Watanabe , K. A. 1988 . Synthesis and reactivity of benzyl 2–0-trifluoromethyl-sulfonyl-beta-D-ribofuranoside and benzyl 3-0-trifluoromethylsulfonyl-beta-D-ribofuranoside—the 1st evidence of trifluoromethyl-sulfonyl (triflyl) migration in carbohydrates . J. Carbohydr. Chem. , 7 : 95 – 114 .
   Web of Science ®Google Scholar
• Pankiewicz , K. W. , Nawrot , B. C. and Watanabe , K. A. 1986 . Nucleosides .137. (Trifluoromethyl)sulfonyl (triflyl) migration—synthesis of 6,3′-anhydro-3-benzyl-1-(5-chloro-5-deoxy-beta-D-xylofuranosyl)barbituri C acid from the 2′-trifluoromethanesulfonate (triflate) of 6,5′-anhydro-3-benzyl-1-beta-D-ribofuranosylbarbituric acid . J. Org. Chem. , 51 : 1525 – 1529 .
   Web of Science ®Google Scholar
• Ogilvie , K. K. and Entwistle , D. W. 1981 . Silyl protecting groups in nucleoside and nucleotide chemistry.15. Isomerization of tert-butyldimethylsilyl protecting groups in ribonucleosides . Carbohydr. Res. , 89 : 203 – 210 .
   Google Scholar
• Kosonen , M. , Hakala , K. and Lonnberg , H. 1998 . Hydrolysis and intramolecular transesterification of ribonucleoside 3′-phosphotriesters: the effect of alkyl groups on the general and specific acid-base-catalyzed reactions of 5′-O-pivaloyluridin-3′-yl dialkyl phosphates . J. Chem. Soc. Perkin Trans. 2 , : 663 – 670 .
   Google Scholar
• Kosonen , M. and Lonnberg , H. 1995 . General and Specific Acid-Base Catalysis of the Hydrolysis and interconversion of ribonucleoside 2′-phosphotriesters and 3′-phosphotriesters—kinetics and mechanisms of the reactions of 5′-O-pivaloyluridine 2′-dimethylphosphates and 3′-dimethylphosphates . J. Chem. Soc. Perkin Trans. 2 , : 1203 – 1209 .
   Google Scholar
• Kosonen , M. , Seppanen , R. , Wichmann , O. and Lonnberg , H. 1999 . Hydrolysis and intramolecular transesterification of ribonucleoside 3′-phosphotriesters: comparison of structural effects in the reactions of asymmetric and symmetric dialkyl esters of 5′-O-pivaloyl-3′-uridylic acid . J. Chem. Soc. Perkin Trans. 2 , : 2433 – 2439 .
   Google Scholar
• Hiratsuka , T. 1976 . Fluorescence properties of 2′ (or 3′)-O-(2,4,6-trinitrophenyl) adenosine 5′-triphosphate and its use in study of binding to heavy-meromyosin ATPase . Biochim. Biophys. Acta , 453 : 293 – 297 .
   PubMedGoogle Scholar
• Azegami , M. and Iwai , K. 1963 . Specific modification of nucleic acids and their constituents with trinitrophenyl group . J. Biochemistry , 55 : 346 – 348 .
   Google Scholar
• Hiratsuk , T. and Uchida , K. 1973 . Preparation and properties of 2′(or 3′)-O-(2,4,6-trinitrophenyl) adenosine 5′-triphosphate, an analog of adenosine-triphosphate . Biochim. Biophys. Acta , 320 : 635 – 647 .
   PubMedGoogle Scholar
• Skarzewski , J. and Skrowaczewska , Z. 1976 . Smiles rearrangement—mechanism of unusual acyl and 2,4-dinitrophenyl migrations in aryl acylamino ethers . Tetrahedron , 32 : 1221 – 1224 .
   Google Scholar
• Okada , K. , Matsui , K. and Sekiguchi , S. 1978 . Aromatic nucleophilic-substitution.10. Confirmation of anionic sigma-complex in base-catalyzed smiles rearrangement of 2-(acetyl-amino)ethyl 2,4-dinitrophenyl ether in dimethyl-sulfoxide . Bull. Chem. Soc. Jap. , 51 : 2601 – 2604 .
   Google Scholar
• Xia , T. B. , SantaLucia , J. , Burkard , M. E. , Kierzek , R. , Schroeder , S. J. , Jiao , X. Q. , Cox , C. and Turner , D. H. 1998 . Thermodynamic parameters for an expanded nearest-neighbor model for formation of RNA duplexes with Watson-Crick base pairs . Biochemistry , 37 : 14719 – 14735 .
   PubMed Web of Science ®Google Scholar
• Levy , A. A. , Rains , H. C. and Smiles , S. 1931 . The rearangement of hydroxysulphones. Part I . J. Chem. Soc. , : 3264 – 3269 .
   Google Scholar