Backbone extended pyrrolidine PNA (bepPNA): A chiral PNA for selective RNA recognition

Tetrahedron

Volumn 62, Issue 10, 2006, Pages 2321-2330

  Govindaraju, T ^a   Kumar, Vaijayanti A ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

bepPNA; Peptide nucleic acids; RNA recognition

Indexed keywords

CARBON; COMPLEMENTARY RNA; NUCLEIC ACID BASE; OLIGOMER; PURINE; PYRIMIDINE; PYRROLIDINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DNA RNA HYBRIDIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 32444437958     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.002     Document Type: Article

References (58)

1. J.C. Barrett, P.S. Miller, and P.O.P. Ts'o Biochemistry 13 1974 4897 4906
2. P.C. Zamecnik, and M.L. Stephenson Proc. Natl. Acad. Sci. U.S.A. 75 1978 280 284
3. M.L. Stephenson, and P.C. Zamecnik Proc. Natl. Acad. Sci. U.S.A. 75 1978 285 289
4. E. Uhlmann, A. Peyman, G. Breipohl, and D.W. Will Angew. Chem., Int. Ed. 37 1998 2796 2823
5. C.F. Bennett C.A. Stein A.M. Craig Applied Antisense Oligonucleotide Technology 1998 Wiley-Liss New York
6. D.A. Braasch, and D.R. Corey Biochemistry 41 2002 4503 4510
7. M. Petersen, and J. Wengel Trends Biotechnol. 21 2003 74 81
8. E. Uhlmann, and A. Peyman Chem. Rev. 90 1990 366 374
9. A. De Mesmaeker, R. Haener, P. Martin, and H.E. Moser Acc. Chem. Res. 28 1995 366 374
10. P.E. Nielsen, M. Egholm, R.H. Berg, and O. Buchardt Science 254 1991 1497 1501
11. B. Hyrup, and P.E. Nielsen Bioorg. Med. Chem. 4 1996 5 23
12. P.E. Nielsen Curr. Opin. Biotechnol. 12 2001 16 20
13. P.E. Nielsen Acc. Chem. Res. 32 1999 624 630
14. P.E. Nielsen, and M. Egholm P.E. Nielsen M. Egholm Peptide Nucleic Acids (PNA). Protocols and Applications 1999 Horizon Scientific Norfolk, CT
15. (f) Nielsen, P. E. Peptide Nucleic Acids: Methods and Protocols; Methods in Molecular Biology; Humana: Totowa, NS, 2002.
16. K.N. Ganesh, and P.E. Nielsen Curr. Org. Chem. 4 2000 1931 1943
17. V.A. Kumar Eur. J. Org. Chem. 2002 2021 2032
18. V.A. Kumar, and K.N. Ganesh Acc. Chem. Res. 38 2005 404 412
19. J. Micklefield Curr. Med. Chem. 8 2001 1157 1179
20. S.M. Freier, and K.-H. Altmann Nucleic Acids Res. 25 1997 4429 4443
21. N.M. Dean Curr. Opin. Biotechnol. 12 2001 622 625
22. D.A. Braasch, and D.R. Corey Chem. Biol. 8 2001 1 7
23. E.T. Kool Chem. Rev. 97 1997 1473 1487
24. A. Eschenmoser, and M. Kisakurek Helv. Chim. Acta 79 1996 1249 1259
25. A. Eschenmoser Science 284 1999 2118 2124
26. A. Puschl, T. Boesen, G. Zuccarello, O. Dahl, and P.E. Nielsen J. Org. Chem. 66 2001 707 712
27. N.K. Sharma, and K.N. Ganesh Chem. Commumn. 2003 2484 2485
28. D.T. Hickman, P.M. King, M.A. Cooper, J. Slater, and M.J. Micklefield Chem. Commun. 2000 2251 2252
29. D.T. Hickman, P.M. King, M.A. Cooper, J. Slater, and M.J. Micklefield Chem. Commun. 2004 516 517
30. A. Puschl, T. Tedeschi, and P.E. Nielsen Org. Lett. 2 2000 4161 4163
31. V.A. Kumar, and Meena Nucleosides Nucleotides Nucleic Acids 22 2003 1285 1288
32. V.A. Kumar, P.S. Pallan, Meena, and K.N. Ganesh Org. Lett. 3 2001 1269 1272
33. K. Schoning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, and A. Eschenmoser Science 290 2000 1347 1351
34. A. Kakefuda, A. Masuda, Y. Ueno, A. Ono, and A. Matsuda Tetrahedron 52 1996 2863 2876
35. N. Katagiri, Y. Morishita, and M. Yamaguchi Tetrahedron Lett. 39 1998 2613 2616
36. N. Katagiri, Y. Morishita, I. Oosawa, and M. Yamaguchi Tetrahedron Lett. 40 1999 6835 6840
37. S. Honzawa, S. Ohwada, Y. Morishita, K. Sato, N. Katagiri, and M. Yamaguchi Tetrahedron 56 2000 2615 2627
38. C.J. Wilds, G. Minasov, F. Natt, P. Von Matt, K.-H. Altamann, and M. Egli Nucleosides Nucleotides Nucleic Acids 20 2001 991 994
39. G.V. Petersen, and J. Wengel Tetrahedron 51 1995 2145 2154
40. A. Chur, B. Holst, O. Dahl, P. Valentin-Hansen, and E.B. Pedersen Nucleic Acids Res. 21 1993 5179 5183
41. A. Lauritsen, and J. Wengel Chem. Commun. 2002 530 531
42. T. Vilaivan, and G. Lowe J. Am. Chem. Soc. 124 2002 9326 9327
43. Meena, and V.A. Kumar Nucleosides Nucleotides Nucleic Acids 22 2003 1101 1104
44. T. Govindaraju, and V.A. Kumar Chem. Commun. 2005 495 497
45. O. Mitsunobu Synthesis 1 1981 1 28
46. J.L. Rabinowitz, and S. Gurin J. Am. Chem. Soc. 75 1953 5758 5759
47. K.A. Cruickshank, F. Jiricny, and C.B. Reese Tetrahedron Lett. 25 1984 681 682
48. M. Egholm, O. Buchardt, and P.E. Nielsen J. Am. Chem. Soc. 114 1992 1895 1897
49. M. Egholm, P.E. Nielsen, O. Buchardt, and R.H. Berg J. Am. Chem. Soc. 114 1992 9677 9678
50. K.L. Dueholm, M. Egholm, C. Behrens, L. Christensen, H.F. Hansen, T. Vulpius, K.H. Petersen, R.H. Berg, P.E. Nielsen, and O. Buchardt J. Org. Chem. 59 1994 5767 5773
51. L. Christensen, R. Fitzpatrick, B. Gildea, K.H. Petersen, H.F. Hansen, T. Koch, M. Egholm, O. Buchardt, P.E. Nielsen, J. Coull, and R.H. Berg J. Pept. Sci. 3 1995 175
52. M.J. Gait Oligonucleotide Synthesis: A Practical Approach 1984 IRL Oxford, UK p 217
53. S. Agrawal S. Agrawal Protocols for Oligonucleotides and Analogs: Synthesis and Properties Methods in Molecular Biology Vol. 20 1993 Humana Totowa, NJ
54. P. Job Ann. Chim. 9 1928 113 203
55. C.R. Cantor, and P.R. Schimmel Biophysical Chemistry Part III 1980 p 624
56. P. Lagriffoule, O. Buchardt, P. Wittung, B. Nordan, K.K. Jensen, and P.E. Nielsen Chem. Eur. J. 3 1997 912 919
57. S.K. Kim, P.E. Nielsen, M. Egholm, O. Buchardt, and R.H. Berg J. Am. Chem. Soc. 115 1993 6477
58. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning: A Laboratory Manual Vol. 2 1989 Cold Spring Harbor Laboratory Cold Spring Harbor, NY