Chiral analogues of peptide nucleic acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy

Tetrahedron

Volumn 55, Issue 1, 1999, Pages 177-192

  Gangamani, Bargur P ^a   Kumar, Vaijayanti A ^a   Ganesh, Krishna N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Chiral analogues; Circular Dichroism; Electronic spectra; Peptide Nucleic Acids

Indexed keywords

4 AMINOPROLYL NUCLEIC ACID; PEPTIDE NUCLEIC ACID; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CIRCULAR DICHROISM; DNA HYBRIDIZATION; DNA SYNTHESIS; MOLECULAR STABILITY; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS; THERMOSTABILITY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0032901654     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01024-2     Document Type: Article

References (36)

1. (a) Nielsen, P. E.; Egholm, M.; Buchardt, O. Science, 1991, 254, 1497.
2. (b) Nielsen, P. E.; Egholm, M.; Buchardt, O. Bioconj. Chem., 1994, 5, 3.
3. (c) Hyrup, B.; Egholm, M.; Nielsen, P. E. BioMed Chem. Lett., 1996, 6, 5.
4. (d) Good, L.; Nielsen, P. E. Antisense & Nucleic Acids Drug. Develop., 1997, 7, 431.
5. (a) Prakash, T. P.; Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. BioMed. Chem. Lett., 1994, 4, 1733,
6. (b) Barawkar, D. A.; Kumar, V. A.; Ganesh, K. N. Nucleic Acids Res., 1996, 24, 1229.
7. (a) Gangamani, B. P.; Kumar, V. A.; Ganesh, K. N. Biochem Biophys. Res. Comm. 1997, 240, 778-784.
8. (b) Kanavarioti, A.; Baird, E. E.; Smith, P. J. J. Org. Chem., 1995, 60, 4873,
9. (c) Baird, E. E.; Dervan, P. J., J. Am. Chem. Soc., 1996, 118, 6141.
10. Kim, S. H.; Nielsen, P. E.; Egholm, O.; Buchardt, O.; Berg, R. H.; Norden, B. J. Am. Chem. Soc., 1993, 115, 6477.
11. Koch, T.; Naesby, M.; Wittung, P.; Jorgensen, M.; Larsson, C.; Buchardt, O.; C.J. Stanley, B. Norden, Nielsen, P. E. Tetrahedron Lett. 1995, 36, 6933.
12. Peterson, K. H.; Jensen, D. K.; Nielsen, P. E.; Egholm, M.; Buchardt, O. BioMed. Chem. Lett., 1995, 5, 1119
13. (b) Bergmann, F.; Bannwarth, W.; Tam, S. Tetrahedron Lett. 1995, 36, 6823.
14. Haaima, G.; Lohse, O.; Buchardt, O.; Nielsen, P. E. Angew. Chem. Int. Ed. Eng. 1996, 35, 1939.
15. Gangamani, B. P.; Kumar, V. A.; Ganesh, K. N. Tetrahedron, 1996, 52, 15017.
16. (a) Stille, J. R.; Frietschel, S. J.; Baker, G. L. J. Org. Chem. 1981, 46, 2954.
17. (b) Peterson, M. L.; Vince, R. J. Med. Chem., 1991, 34, 2787.
18. Jordan, S.; Schwemler, C.; Winfried, K.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. BioMed. Chem. Lett., 1997, 7, 681 and ibid,687.
19. Jordan, S.; Schwemler, C.; Winfried, K.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. BioMed. Chem. Lett., 1997, 7, 681 and ibid 687.
20. (a) Lowe, G.; Vilaivan, T. J. Chem. Soc. Perkin Trans I, 1997, 539.
21. (b) Lowe, G.; Vilaivan, T.; J. Chem. Soc. Perkin Trans. I, 1997, 547.
22. (c) Lowe, G.; Vilaivan, T.; J. Chem. Soc. Perkin Trans I, 1997, 555.
23. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I., Anal. Biochem., 1970, 34, 595.
24. Sinha, N. D.; Biernat, J.; McManus, J., Koster, H. Nucleic Acids Res., 1984, 12, 4539.
25. Ceulemans, G.; Aerschot, A. V.; Wrobloski, B.; Rozenski, J.; Hendrix, C.; Heredewijn, P. Chem. Eur. J., 1997, 3, 1997.
26. Tomac, S.; Sarkar, M.; Ratilainen, T.; Wittung, P.; Nielsen, P. E.; Norden, B.; Graslund, A. J. Am. Chem. Soc., 1996, 118, 5514.
27. Uhlmann, E.; Will, D. W.; Breipohl, G.; Longner, D.; Ryte, A. Angew. Chem. Int. Ed. Eng., 1996, 35, 2632.
28. Gray, D. M.; Ratliff, R. L.; Waughan, M. R. Methods Enzymol., 1992, 211, 389
29. Gray, D. M.; Hung, S. -H.; Johnson, K. H. Methods Enzymol., 1995, 246, 19.
30. Wittung, P.; Nielsen, P. E.; Buchardt, O.; Egholm, M.; Norden, B. Nature, 1994, 368, 561.
31. Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc., 1995, 117, 10167
32. Hodges, R. S.; Merrifield, R. B. Anal. Biochem., 1975, 65, 241
33. Merrifield, R. B.; Stewart, J. M.; Jernberg, N. Anal. Biochem., 1966, 38, 1905.
34. Dueholm, K. L.; Egholm, M.; Behrens, C.; Christensen, L.; Hansen, H. F.; Vulpius, T.; Peterson, K. H.; Berg, R. H.; Nielsen, P. E.; Buchardt, O. J. Org. Chem., 1994, 59, 5767.
35. Erickson, B. W.; Merrifield, R. B. Solid phase peptide Synthesis in The Proteins, Vol II, Ed. H. Neurath and R. L. Hills, Academic Presss, NY, 1976, p 255.
36. NCL Communication Number 6446