Synthesis and Hybridization Properties of Oligonucleotides Containing (2S,3R)-9-(2,3,4-Trihydroxybutyl)Adenine

REFERENCES

• Uhlmann , E. and Peyman , A. 1990 . Antisense oligonucleotides: A new therapeutic principle . Chemical Reviews , 90 : 544 – 584 . [CSA]
   Web of Science ®Google Scholar
• Milligan , J. F. , Matteucci , M. D. and Martin , J. C. 1993 . Current concepts in antisense drug design . Journal of Medicinal Chemistry , 36 : 1923 – 1937 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Branch , A. D. 1998 . A good antisense molecule is hard to find . Trends in Biochemical Science , 23 : 45 – 50 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Stein , C. A. 1999 . Keeping the biotechnology of antisense in context . Nature Biotechnology , 17 : 209 [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Mesmaeker , A. D. , Altmann , K. -H. , Waldner , A. and Wendeborn , S. 1995 . Backbone modifications in oligonucleotides and peptides nucleic acid systems . Current Opinion in Structural Biology , 5 : 343 – 355 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Nielsen , P. E. , Egholm , M. , Berg , R. H. and Buchardt , O. 1991 . Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide . Science , 254 : 1497 – 1500 . [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Ueno , Y. , Kato , Y. , Okatani , S. , Ishida , N. , Nakanishi , M. and Kitade , Y. 2003 . Synthesis of antisense oligonucleotides carrying modified 2-5A molecules at their 5′-termini and their properties . Bioconjugate Chemistry , 14 : 690 – 696 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Ito , T. , Ueno , Y. , Komatsu , Y. and Matsuda , A. 2003 . Synthesis, thermal stability and resistance to enzymatic hydrolysis of the oligonucleotides containing 5-(N-aminohexyl)carbamoyl-α−O-methyluridines . Nucleic Acids Research , 31 : 2514 – 2523 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kanazaki , M. , Ueno , Y. , Shuto , S. and Matsuda , A. 2000 . Highly nuclease-resistant phosphodiester-type oligodeoxynucleotides containing 4′α−C-aminoalkylthymidines form thermally stable duplexes with DNA and RNA. A candidate for potent antisense molecules . Journal of the American Chemical Society , 122 : 2422 – 2432 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Haginoya , N. , Ono , A. , Nomura , Y. , Ueno , Y. and Matsuda , A. 1997 . Synthesis of oligodeoxyribonucleotides containing 5-(N-aminoalkyl)carbamoyl-2′-deoxyuridines by a new postsynthetic modification method and their thermal stability and nuclease-resistance properties . Bioconjugate Chemistry , 8 : 271 – 280 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Obika , S. , Nanbu , D. , Hari , Y. , Andoh , J. , Morio , K. , Doi , T. and Imanishi , T. 1998 . Stability and structural features of the duplexes containing nucleoside analogs with a fixed N-type conformation, 2′-O,4′-C-methyleneribonucleosides . Tetrahedron Letters , 39 : 5401 – 5404 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Koshkin , A. A. , Nielsen , P. , Meldgaard , M. , Rajwanshi , V. K. , Singh , S. K. and Wengel , J. 1998 . LNA (locked nucleic acid): An RNA mimic forming exceedingly stable LNA:LNA duplexes . Journal of the American Chemical Society , 120 : 13252 – 13253 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Schneider , K. C. and Benner , S. A. 1990 . Oligonucleotides containing flexible nucleoside analogs . Journal of the American Chemical Society , 112 : 453 – 455 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Augustyns , K. , Van Aerschot , A. , Van Schepdael , A. , Urbanke , C. and Herdewijn , P. 1991 . Influence of the incorporation of (S)-9-(3,4-dihydroxybutyl)adenine on the enzymic stability and base-pairing properties of oligodeoxynucleotides . Nucleic Acids Research , 19 : 2587 – 2593 . [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Azymah , M. , Chavis , C. , Lucas , M. , Morvan , F. and Imbach , J. -L. 1992 . Isotactic glycero oligothymidylate. A convenient preparation of (R)- and (S)-1′,2′-seco-2′-nor-thymidine . Nucleosides & Nucleotides , 11 : 1241 – 1255 . [INFOTRIEVE] [CSA]
   Web of Science ®Google Scholar
• Nielsen , P. , Kirpekar , F. and Wengel , J. 1994 . Incorporation of (R)- and (S)-3′,4′-seco-thymidine into oligodeoxynucleotides: Hybridization properties and enzymic stability . Nucleic Acids Research , 22 : 703 – 710 . [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Nielsen , P. , Dreiøe , L. H. and Wengel , J. 1995 . Synthesis and evaluation of oligodeoxynucleotides containing acyclic nucleosides: Introduction of three novel analogs and a summary . Bioorganic and Medicinal Chemistry , 3 : 19 – 28 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kværnø , L. , Kumar , R. , Dahl , B. M. , Olsen , C. E. and Wengel , J. 2000 . Synthesis of abasic locked nucleic acid and two seco-LNA derivatives and evaluation of their hybridization properties compared with their more flexible DNA counterparts . Journal of Organic Chemistry , 65 : 5167 – 5176 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Merle , Y. , Bonneil , E. , Merle , L. , Sági , J. and Szemzö , A. 1995 . Acyclic oligonucleotide analogues . International Journal of Biological Macromolecules , 17 : 239 – 246 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMedGoogle Scholar
• Obika , S. , Takashima , Y. , Matsumoto , Y. , Shimoyama , A. , Koishihara , Y. , Ohsugi , Y. , Doi , T. and Imanishi , T. 1996 . Properties of novel oligonucleotide analogues containing an acyclic nucleosides and a carbamate linkage . Bioorganic & Medicinal Chemistry Letters , 6 : 1357 – 1360 . [INFOTRIEVE] [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Peng , L. and Roth , H. -J. 1997 . Synthesis and properties of 2′-deoxy-1′,2′-seco-D-ribosyl (5′ → 3′)oligonucleotides (= 1′,2′-seco-DNA) containing adenine and thymine . Helvetica Chimica Acta , 80 : 1494 – 1512 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Benhida , R. , Devys , M. , Fourrey , J. -L. , Lecubin , F. and Sun , J. -S. 1998 . Incorporation of serinol derived acyclic nucleoside analogues into oligonucleotides: influence on duplex and triplex formation . Tetrahedron Letters , 39 : 6167 – 6170 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Rana , V. S. , Kumar , V. A. and Ganesh , K. N. 2001 . Oligonucleotides with (N-thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility . Tetrahedron , 57 : 1311 – 1321 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Zhang , L. , Peritz , A. and Meggers , E. 2005 . A simple glycol nucleic acid . Journal of the American Chemical Society , 127 : 4174 – 4175 . [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Koga , M. , Tamai , K. , Ueda , M. , Uchida , T. , Yamamuro , T. , Suzuki , T. and Saeki , T. 2001 . Structure and properties of carbocyclic 5′-nor oligodeoxynucleotides . Nucleic Acids Research, , 1 : 19 – 20 . Suppl.[CSA]
   Google Scholar
• Schöning , K. -U. , Scholz , P. , Guntha , S. , Wu , X. , Krishnamurthy , R. and Eschenmoser , A. 2000 . Chemical etiology of nucleic acid structure: the α -threofuranosyl-(3′ → 2′) oligonucleotide system . Science , 290 : 1347 – 1351 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kitade , Y. , Hirota , K. and Maki , Y. 1993 . Reductive cleavage of the ribose moiety in purine nucleosides using diisobutylaluminum hydride: a new method for the preparation of acyclonucleosides . Tetrahedron Letters , 34 : 4835 – 4836 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Hirota , K. , Monguchi , Y. , Sajiki , H. , Sako , M. and Kitade , Y. 1998 . Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines . Perkin Transactions , 1 : 941 – 946 . [CSA] [CROSSREF]
   Google Scholar
• Beaucage , S. L. and Caruthers , M. H. 1981 . Deoxynucleoside phosphoramidites. A new class of key intermediates for deoxypolynucleotide synthesis . Tetrahedron Letters , 22 : 1859 – 1862 . [CSA] [CROSSREF]
   Web of Science ®Google Scholar
• Gait , M. J. , ed. 1984 . Oligonucleotides Synthesis: A Practical Approach , Oxford , U. K. : IRL Press .
   Google Scholar
• Marky , L. A. and Breslauer , K. L. 1987 . Calculating thermodynamic data for transitions of any molecularity from equilibrium melting curves . Biopolymer , 26 : 1601 – 1620 . [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Puglisi , J. D. and Tinoco , I. Jr. 1989 . “ Absorbance melting curves of RNA ” . In Methods in Enzymology , Edited by: Dahlberg , J. E. and Abelson , J. N. Vol. 180 , 304 – 325 . San Diego : Academic Press .
   Google Scholar