47
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Novel 2′-Deoxy Type Trans-3′,4′-Bridged Nucleic Acid

, , , , , , & show all
Pages 1079-1082 | Published online: 10 Dec 2007

REFERENCES

  • Tarköy , M. , Bolli , M. , Schweizer , B. and Leumann , C. 1993 . Nucleic-acid analogues with constraint conformational flexibility in the sugar–phosphate backbone (‘Bicyclo-DNA’) Part 1 . Helv. Chim. Acta , 76 : 481 – 510 .
  • Tarköy , M. , Bolli , M. and Leumann , C. 1994 . Nucleic-acid analogues with constraint conformational flexibility in the sugar–phosphate backbone (‘Bicyclo-DNA’) Part 3 . Helv. Chim. Acta , 77 : 716 – 744 .
  • Bolli , M. , Trafelet , H. U. and Leumann , C. 1996 . Watson-Crick base-pairing properties of bicycle-DNA . Nucleic Acids Res. , 24 : 4660 – 4667 .
  • Steffens , R. and Leumann , C. J. 1997 . Tricyclo-DNA: A phosphodiester-backbone based DNA analog exhibiting strong complementary base-pairing properties . J. Am. Chem. Soc. , 119 : 11548 – 11549 .
  • Steffens , R. and Leumann , C. 1997 . Nucleic-acid analogs with constraint conformational flexibility in the sugar-phospate backbone ‘Tricyclo-DNA’ Part 1 . Helv. Chim. Acta , 80 : 2426 – 2439 .
  • Steffens , R. and Leumann , C. J. 1999 . Synthesis and thermodynamic and biophysical properties of tricyclo-DNA . J. Am. Chem. Soc. , 121 : 3249 – 3255 .
  • Nielsen , P. , Pfundheller , H. M. , Olsen , C. E. and Wengel , J. 1997 . Synthesis of 2′-O,3′-C-linked bicyclic nucleosides and bicyclic oligonucleotides . J. Chem. Soc., Perkin Trans. 1 , : 3423 – 3433 .
  • Ravn , J. , Thorup , N. and Nielsen , P. 2001 . A conformationally locked tricyclic nucleoside. Synthesis, crystal structure and incorporation into oligonucleotides . J. Chem. Soc., Perkin Trans. 1 , : 1855 – 1861 .
  • Vijgen , S. , Nauwelaerts , K. , Wang , J. , Aerhot , A. V. , Lagoja , I. and Herdewijn , P. 2005 . Synthesis and conformational analysis of a ribo-type cyclohexenyl nucleoside . J. Org. Chem. , 70 ( 12 ) : 4591 – 4597 .
  • Obika , S. , Sekiguchi , M. , Osaki , T. , Shibata , N. , Masaki , M. , Hari , Y. and Imanishi , T. 2002 . Synthesis and conformation of a novel bridged nucleoside with S-type sugar puckering, trans-3′,4′-BNA monomer . Tetrahedron Lett. , 43 : 4365 – 4368 . P. Nielsen's group also reported the synthesis of 3 independently, and reference to Chem. Commun. 2002, 1888–1889
  • Sekiguchi , M. , Osaki , T. , Harada , Y. , Obika , S. and Imanishi , T. 2003 . Trans-3′,4′-BNAs, novel nucleic acid analogues with an S-type conformation: Synthesis and incorporation into oligonucleotides . Nucleic Acids Res. Suppl. , 3 : 111 – 112 .
  • Sekiguchi , M. , Obika , S. , Harada , Y. , Osaki , T. , Sommjing , R. , Mitsuoka , Y. , Shibata , Y. , Masaki , M. and Imanishi , T. 2006 . Synthesis and properties of trans-3′,4′-bridged nucleic acids having typical S-type sugar conformation . J. Org. Chem. , 71 ( 4 ) : 1306 – 1316 .
  • Obika , S. , Osaki , T. , Sekiguchi , M. , Sommjing , R. , Harada , Y. and Imanishi , T. 2004 . Synthesis and conformation of a novel bridged nucleic acid having a trans-fused 3,5,8-trioxabicyclo[5.3.0]decane structure . Tetrahedron Lett. , 45 : 4801 – 4804 .
  • Froehlich , M. L. , Swartling , D. J. , Lind , R. E. , Mott , A. W. and Bergstrom , D. E. 1989 . An improved synthesis of 3′-keto-5′-O-tritylthymidine . Nucleosides Nucleotides , 8 : 1529 – 1535 .
  • Sharma , M. and Bobek , M. 1990 . Synthesis of 2′,3′-dideoxy-3′-methylene pyrimine nucleosides as anti-AIDS agents . Tetrahedron Lett. , 31 : 5839 – 5842 .
  • The direct benzylation of 6 under various conditions did not give 9 effectively

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.