Efficient conjugation of peptides to oligonuoleotides by 'native ligation'

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4900-4908

  Stetsenko, Dmitry A ^a   Gait, Michael J ^a  

^a MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PEPTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; POLYPEPTIDE; THIOESTER;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEOTIDE SEQUENCE; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; OLIGONUCLEOTIDES; PEPTIDES; TRIFLUOROACETIC ACID;

EID: 0034637593     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000214z     Document Type: Article

References (51)

1. Antisense research and applications; Crooke, S. T., Lebleu, B., Ed.; CRC Press: Boca Raton, 1993.
2. Chadwick, D. J.; Cardew, G. Oligonucleotides as therapeutic agents; John Wiley: Chichester, 1997.
3. Crooke, S. T. J. Drug Targeting 1995, 3, 185-190.
4. Stein, C. A.; Narayan, R. Perspect. Drug Discovery Design 1996, 4, 41-50.
5. Morris, M. C.; Vidai, P.; Chaloin, L.; Heitz, F.; Divita, G. Nucl. Acids Res. 1997, 25, 2730-2736.
6. Dokka, S.; Toledo-Velasquez, D.; Shi, X.; Wang, L.; Rojanasukul, Y. Pharmaceut. Res. 1997, 14, 1759-1764.
7. Wyman, T. B.; Nicol, F.; Zelphati, O.; Scario, P. V.; Plank, C.; Szoka, F. C. Biochemistry 1997, 36, 3008-3017.
8. Wadhwa, M. S.; Collard, W. T.; Adami, R. C.; Mckenzie, D. L.; Rice, K. G. Bioconjugate Chem. 1997, 8, 81-88.
9. Pichon, C.; Freulon, I.; Midoux, P.; Mayer, R.; Monsigny, M.; Roche, A.-M. Antisense and Nucl. Acid Drug. Dev. 1997, 7, 335-343.
10. Bachmann, A. S.; Surovoy, A.; Jung, G.; Moelling, K. J. Mol. Med. 1998, 76, 126-132.
11. Midoux, P.; Kichler, A.; Boutin, V.; Maurizot, J.-C.; M., M. Bioconj. Chem. 1998, 9, 260-267.
12. Vivès, E.; Lebleu, B. Tetrahedron Lett. 1997, 38, 1183-1186.
13. Derossi, D.; Joliot, A. H.; Chassaing, G.; Prochiantz, A. J. Biol. Chem. 1994, 269, 10444-10450.
14. Pichon, C.; Arar, K.; Stewart, A. J.; Dodon, M. D.; Gazzolo, L.; Courtoy, P. J.; Mayer, R.; Monsigny, M.; Roche, A.-C. Mol. Pharmacol. 1997, 51, 431-438.
15. Chaloin, L.; Vidai, P.; Lory, P.; Méry, J.; Lautredou, N.; Divita, G.; Heitz, F. Biochem. Biophys. Res. Comm. 1998, 243, 601-608.
16. Antopolsky, M.; Azhayeva, E.; Tengvall, U.; Auriola, S.; Jääskeläinen, I.; Rönkkö, S.; Honkakoski, P.; Urtti, A.; Lönnberg, H.; Azhayev, A. Bioconjugate Chem. 1999, 10, 598-606.
17. Haralambidis, J.; Duncan, L.; Angus, K.; Tregear, G. W. Tetrahedron Lett. 1987, 28, 5199-5202.
18. Juby, C. D.; Richardson, C. D.; Brousseau, R. Tetrahedron Lett. 1991, 32, 879-882.
19. de La Torre, B. G.; Avino, A.; Tarrason, G.; Piulats, J.; Albericio, F.; Eritja, R. Tetrahedron Lett. 1994, 35, 2733-2736.
20. Truffert, J.-C.; Lorthoir, O.; Asseline, U.; Thuong, N. T.; Brack, A. Tetrahedron Lett. 1994, 35, 2353-2356.
21. Bergmann, F.; Bannwarth, W. Tetrahedron Lett. 1995, 36, 1839-1842.
22. Basu, S.; Wickstrom, E. Tetrahedron Lett. 1995, 36, 4943-4946.
23. Tetzlaff, C. N.; Schwope, I.; Bleczinski, C. F.; Steinberg, J. A.; Richert, C. Tetrahedron Lett. 1998, 39, 4215-4218.
24. De Napoli, L.; Messere, A.; Montesarchio, D.; Piccialli, G.; Benedetti, E.; Bucci, E.; Rossi, F. Bioorg. Med. Chem. 1999, 7, 395-400.
25. Schwope, I.; Bleczinski, C. F.; Richert, C. J. Org. Chem. 1999, 64, 4749-4761.
26. Eritja, R.; Pons, A.; Escarceller, M.; Giralt, E.; Albericio, F. Tetrahedron 1991, 47, 4113-4120.
27. Bongartz, J. P.; Aubertin, A. M.; Milhaud, P. G.; Lebleu, B. Nucl. Acids Res. 1994, 22, 4681-4688.
28. Tung, C.-H.; Rudolph, M. J.; Stein, S. Bioconjugate Chem. 1991, 2, 464-465.
29. Harrison, J. G.; Balasubramanian, S. Nucl. Acids Res. 1998, 26, 3136-3145.
30. Soukchareun, S.; Haralambidis, J.; Tregear, G. Bioconjugate Chem. 1998, 9, 466-475.
31. Arar, K.; Aubertin, A.-M.; Roche, A.-C.; Monsigny, M.; Mayer, M. Bioconjugate Chem. 1995, 6, 573-577.
32. McMinn, D. L.; Greenberg, M. M. Bioorg. Med. Chem. Lett. 1999, 9, 547-550.
33. Kahl, J. D.; Greenberg, M. M. J. Org. Chem. 1999, 64, 507-510.
34. Grandas, A.; Robles, J.; Pedroso, E. Nucleosides Nucleotides 1995, 14, 825-828.
35. Peyrottes, S.; Mestre, B.; Burlina, F.; Gait, M. J. Tetrahedron 1998, 54, 12513-12522.
36. Peyrottes, S.; Mestre, B.; Burlina, F.; Gait, M. J. Nucleosides Nucleotides 1999, 18, 1443-1448.
37. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
38. Wilken, J.; Kent, S. B. H. Curr. Opin. Biotech. 1998, 9, 412-426.
39. Canne, L. E.; Botti, P.; Simon, R. J.; Chem, Y.; Dennis, E. A.; Kent, S. B. H. J. Am. Chem. Soc. 1999, 121, 8720-8727.
40. Bruick, R. K.; Dawson, P. E.; Kent, S. B. H.; Usman, N.; Joyce, G. F. Chem. Biol. 1996, 3, 49-56.
41. McPherson, M.; Wright, M. C.; Lohse, P. A. Synlett 1999, S1, 978-980.
42. Canne, L. E.; Walker, S. M.; Kent, S. H. B. Tetrahedron Lett. 1995, 36, 1217-1220.
43. Hackeng, T. M.; Griggin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10068-10073.
44. Li, X.; Kawakami, T.; Aimoto, S. Tetrahedron Lett. 1998, 39, 8669-8672.
45. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374.
46. Burns, J. A.; Butler, J. C.; Moran, J.; Whitesides, G. M. J. Org. Chem. 1991, 56, 2648-2650.
47. Dawson, P. E.; Churchill, M. J.; Ghadri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
48. Shin, Y.; Wianans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689.
49. Atherton, E.; Sheppard, R. C. Solid-phasepeptide synthesis: A practical approach; Oxford University Press: Oxford, 1989.
50. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-202.
51. Brown, T.; Brown, D. J. S. In Oligonucleotides and Analogues: A Practical Approach; Eckstein, F., Ed.; OUP: Oxford, 1991; pp 1-24.