trans-5-aminopipecolyl-aegPNA chimera: Design, synthesis, and study of binding preferences with DNA/RNA in duplex/triplex mode

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6956-6959

  Lonkar, Pallavi S ^a   Kumar, Vaijayanti A ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; DERIVATIVES; DNA; RNA; SYNTHESIS (CHEMICAL);

CHIMERAS; TRANS EQUATORIAL DISPOSITION; TRANS-5-AMINOPIPECOLIC ACID;

MONOMERS;

DOUBLE STRANDED DNA; DOUBLE STRANDED RNA; MONOMER; PEPTIDE NUCLEIC ACID; PIPECOLIC ACID DERIVATIVE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHIMERA; DRUG CONFORMATION; DRUG DESIGN; DRUG DNA BINDING; DRUG SYNTHESIS; HYBRIDIZATION; REACTION ANALYSIS; RNA BINDING; TRANS ISOMER;

DNA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDE NUCLEIC ACIDS; RNA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 23644433006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0506884     Document Type: Article

References (35)

1. Nielsen, P. E.; Egholm, M.; Berg, R. H.; Buchardt, O. Science 1991, 254, 1497-1501.
2. Egholm, M.; Buchardt, O.; Christensen, L.; Behrens, C.; Freier, S. M.; Driver, D. A.; Berg, R. H.; Kim, S. K.; Norden, B.; Nielsen, P. E. Nature 1993, 365, 566-568.
3. Koppelhus, U.; Nielsen, P. E. Adv. Drug Delivery Rev. 2003, 55, 267-280.
4. Uhlmann, E.; Peyman, A.; Breipohl, G.; Will, W. D. Angew. Chem., Int. Ed. 1998, 37, 2796-2823.
5. Hyrup, B.; Egholm, M.; Nielsen, P. E.; Wittung, P.; Norden, B.; Buchardt, O. J. Am. Chem. Soc. 1994, 116, 7964-7970.
6. Petersen, M.; Wengel, J. Trends Biotechnol. 2003, 21, 74-81.
7. Lescrinier, E.; Esnouf, R.; Schraml, J.; Bussen, R.; Heus, H. A.; Hilbers, C. W.; Herdewijn, P. Chem. Biol. 2000, 7, 719-731.
8. Wang, J.; Verbeure, B.; Luyten, I.; Lescrinier, E.; Froeyen, M.; Hendrix, C.; Rosemeyer, H.; Seela, F.; Aerschot, A. V.; Herdewijn, P. J. Am. Chem. Soc. 2000, 122, 8595-8602.
9. Kozlov, I. A.; Zielinski, M.; Allart, B.; Kerremans, L.; Aerschot, A. V.; Bussen, R.; Herdewijn, P.; Orgel, L. E. Chem. Eur. J. 2000, 6, 151-155.
10. (a) Betts, I.; Josey, J. A.; Veal, J. M.; Jorden, S. R. Science 1995, 270, 1838-1841
11. (b) Ericksson, M.; Nielsen, P. E. Nat. Struct. Biol. 1996, 3, 410-413.
12. (c) Brown, S. C.; Thomson, S. A.; Veal, J. M.; Davis, D. J. Science 1994, 265, 777-780.
13. (a) Kumar, V. A. Eur. J. Org. Chem. 2002, 2021-2032.
14. (b) Govindaraju, T.; Kumar V. A.; Ganesh, K. N. Chem. Commun. 2004, 860-861.
15. (c) Shirude, P. S.; Kumar V. A.; Ganesh, K. N. Terahedron Lett. 2004, 45, 3085-3088.
16. (d) Govindaraju, T.; Gonnade, R. G.; Bhadbhade, M. M.; Kumar V. A.; Ganesh, K. N. Org. Lett. 2003, 5, 3013-3016.
17. (e) Kumar V. A.; Ganesh, K. N. Acc. Chem. Res. 2005, 38, 404-412.
18. Gangamani, B. P.; Kumar, V. A.; Ganesh, K. N. Tetrahedron 1999, 57, 177-192
19. Lonkar, P. S.; Kumar, V. A.; Ganesh, K. N. Nucleosides Nucleotides and Nucleic Acids 2001, 20, 1197-1200.
20. Lonkar, P. S.; Kumar, V. A. Bioorg. Med. Chem. Lett. 2004, 14, 2147-2149.
21. Adams, D. R.; Bailey, P. D.; Collier, I. D.; Hefferman, J. D.; Stokes, S. Chem. Commun. 1996, 349-350.
22. (a) Puschl, A.; Boesen, T.; Tedeschi, T.; Dahl, O.; Nielsen, P. E. J. Chem. Soc., Perkin Trans. 1 2001, 2757-2763.
23. (b) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687-692.
24. (c) Lagriffoule, P.; Wittung, P.; Eriksson, M.; Jensen, K. K.; Norden, B.; Buchardt, O.; Nielsen, P. E. Chem. Eur. J. 1997, 3, 912-919.
25. Nielsen, P. E.; Egholm, M.; Berg, R. H.; Buchardt, O. Bioconjugate Chem. 1994, 5, 3-7.
26. Shirude, P. S.; Kumar, V. A.; Ganesh, K. N. Tetrahedron 2004, 60, 9485-9491.
27. Lowe, G.; Vilaivan, T.J. Chem. Soc., Perkin Trans. 1 1997, 547-554.
28. Nielsen, P. E.; Egholm, M. Peptide Nucleic Acids: Protocols and Applications; Horizon Scientific Press: Norfolk, England, 1999.
29. Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202-4207.
30. (a) Job, P. Ann. Chim. 1928, 9, 113-203.
31. (b) Cantor, C. R.; Schimmel, P. R. Biophys. Chem. 1980, Part III, 624pp.
32. (a) Slaitas, A.; Yeheskiely, E. Eur. J. Org Chem. 2002, 2391-2399.
33. (b) Myers, M. C.; Witschi, M. A.; Larionova, N. V.; Franck, J. M.; Haynes, R. D.; Hara, T.; Grajkowski, A.; Appella, D. H. Org. Lett. 2003, 5, 2695-2698.
34. (c) Govindaraju T.; Kumar, V. A.; Ganesh, K. N. J. Org. Chem. 2004, 69, 1858-1865.
35. (d) Samuel, T. H.; David, T.; Hickman, T.; Morral, J.; Beadham, G.; Micklefield, J. Chem. Comm. 2004, 516-517.