Synthesis and properties of isobicyclo-DNA

Chemistry - A European Journal

Volumn 19, Issue 22, 2013, Pages 6990-7006

  Gerber, Anna Barbara ^a   Leumann, Christian J ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

DNA; nucleosides; oligonucleotides; RNA; serum stability

Indexed keywords

BIOCHEMICAL TESTS; BIOLOGICAL PROPERTIES; BUILDING BLOCKES; CD SPECTROSCOPY; FETAL BOVINE SERUM; MODIFIED OLIGONUCLEOTIDES; NUCLEOSIDES; SERUM STABILITY;

CIRCULAR DICHROISM SPECTROSCOPY; OLIGONUCLEOTIDES; RNA;

DNA;

DNA; OLIGONUCLEOTIDE; RIBONUCLEASE H; RNA;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; METABOLISM; NUCLEOTIDE SEQUENCE; SYNTHESIS;

BASE SEQUENCE; CIRCULAR DICHROISM; DNA; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; RIBONUCLEASE H; RNA;

EID: 84878112207     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300487     Document Type: Article

References (39)

1. J. Kurreck, Angew. Chem. 2009, 121, 1404-1426
2. Angew. Chem. Int. Ed. 2009, 48, 1378-1398.
3. C. F. Bennett, E. E. Swayze, Annu. Rev. Pharmacol. Toxicol. 2010, 50, 259-293.
4. The ENCODE project consortium, Nature 2012, 489, 57-74.
5. J. C. vanDeutekom, A. A. Janson, I. B. Ginjaar, W. S. Frankhuizen, A. Aartsma-Rus, M. Bremmer-Bout, J. T. denDunnen, K. Koop, A. J. vanderKooi, N. M. Goemans, S. J. deKimpe, P. F. Ekhart, E. H. Venneker, G. J. Platenburg, J. J. Verschuuren, G. J. vanOmmen, N. Engl. J. Med. 2007, 357, 2677-2686
6. M. Manoharan, Biochim. Biophys. Acta Gene Struct. Expression 1999, 1489, 117-130.
7. H. M. Moulton, J. D. Moulton, Biochim. Biophys. Acta Biomembr. 2010, 1798, 2296-2303.
8. M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Norden, P. E. Nielsen, Nature 1993, 365, 566-568.
9. S. K. Singh, P. Nielsen, A. A. Koshkin, J. Wengel, Chem. Commun. 1998, 455-456
10. S. Obika, D. Nanbu, Y. Hari, J. I. Andoh, K. I. Morio, T. Doi, T. Imanishi, Tetrahedron Lett. 1998, 39, 5401-5404.
11. M. Bolli, H. U. Trafelet, C. Leumann, Nucleic Acids Res. 1996, 24, 4660-4667
12. M. Tarköy, M. Bolli, C. Leumann, Helv. Chim. Acta 1994, 77, 716-744
13. M. Tarköy, C. Leumann, Angew. Chem. Int. Ed. Engl. 1993, 32, 1432-1434
14. P. Silhár, C. J. Leumann, Bioorg. Med. Chem. 2010, 18, 7786-7793.
15. D. Renneberg, C. Leumann, J. Am. Chem. Soc. 2002, 124, 5993-6002
16. S. Murray, D. Ittig, E. Koller, A. Berdeja, A. Chappell, T. P. Prakash, M. Norrbom, E. E. Swayze, C. J. Leumann, P. P. Seth, Nucleic Acids Res. 2012, 40, 6135-6143
17. J. Lietard, C. J. Leumann, J. Org. Chem. 2012, 77, 4566-4577.
18. R. Steffans, C. Leumann, Helv. Chim. Acta 1997, 80, 2426-2439.
19. R. Meier, S. Grüschow, C. J. Leumann, Helv. Chim. Acta 1999, 82, 1813-1828.
20. X.-F. Zhu, H. J. Williams, A. I. Scott, J. Chem. Soc. Perkin Trans. 1 2000, 2305-2306.
21. J. H. vandeSande, N. B. Ramsing, M. W. Germann, W. Elhorst, B. W. Kalisch, E. vonKitzing, R. T. Pon, R. C. Clegg, T. M. Jovin, Science 1988, 241, 551-557.
22. C. Hendrix, H. Rosemeyer, I. Verheggen, F. Seela, A. VanAerschot, P. Herdewijn, Chem. Eur. J. 1997, 3, 110-120.
23. A. K. Shchyolkina, Y. P. Lysov, I. A. Ilichove, A. A. Chernyi, Y. B. Golova, B. K. Chernov, B. P. Gottikh, V. L. Florentiev, FEBS Lett. 1989, 244, 39-42
24. A. K. Shchyolkina, O. F. Borisova, M. A. Livshits, G. E. Pozmogova, B. K. Chernov, R. Klement, T. M. Jovin, Biochemistry 2000, 39, 10034-10044.
25. M. Petersheim, D. H. Turner, Biochemistry 1983, 22, 256-263.
26. G. S. Manning, Acc. Chem. Res. 1979, 12, 443-449.
27. Circular Dichroism: Principles and Applications, 2 nd ed. (Eds.:, N. Berova, K. Nakanishi, R. W. Woody,), Wiley, New York, 2002.
28. L. Bellon, J.-L. Barascut, G. Maury, G. Divita, R. Goody, J.-L. Imbach, Nucleic Acids Res. 1993, 21, 1587-1593.
29. J. Wang, B. Verbeure, I. Luyten, E. Lescrinier, M. Froeyen, C. Hendrix, H. Rosemeyer, F. Seela, A. vanAerschot, P. Herdewijn, J. Am. Chem. Soc. 2000, 122, 8595-8602.
30. J. Kypr, I. Kejnovska, D. Renciuk, M. Vorlickova, Nucleic Acids Res. 2009, 37, 1713-1725.
31. M. Vorlickova, J. Kypr, V. Sklenar, A. Klug, J. Mol. Biol. 1983, 166, 85-92.
32. N. G. A. Abrescia, A. Thompson, T. Huynh-Dinh, J. A. Subirana, Proc. Natl. Acad. Sci. USA 2002, 99, 2806-2811.
33. A. K. Shchyolkina, O. F. Borisova, M. A. Livshits, T. M. Jovin, J. Mol. Biol. 2003, 37, 223-231
34. C. Otto, G. A. Thomas, T. M. Jovin, W. L. Peticolas, Biochemistry 1991, 30, 3062-3069.
35. W. F. Lima, S. T. Crooke, Biochemistry 1997, 36, 390-398
36. W. F. Lima, V. Mohan, J. Biol. Chem. 1997, 272, 18191-18199.
37. E. Zamaratski, P. I. Pradeepkumar, J. Chattopadhyaya, J. Biochem. Biophys. Methods 2001, 48, 189-208.
38. D. Yu, R. P. Iyer, D. R. Shaw, J. Lisziewicz, Y. Li, Z. Jiang, A. Roskey, S. Agrawal, Bioorg. Med. Chem. 1996, 4, 1685-1692.
39. C. Wahlestedt, P. Salmi, L. Good, J. Kela, T. Johnsson, T. Hökfelt, C. Broberger, F. Porreca, J. Lai, K. Ren, M. Ossipov, A. Koshkin, N. Jakobsen, J. Skouv, H. Oerum, M. H. Jacobsen, J. Wengel, Proc. Natl. Acad. Sci. USA 2000, 97, 5633-5638.