Synthesis of symmetric fluorescently labeled poly(ethylene glycols) using phosphoramidites of pyrenebutanol and their characterization by MALDI mass spectrometry

Macromolecules

Volumn 29, Issue 9, 1996, Pages 3060-3072

  Lee, Sam ^a   Winnik, Mitchell A ^a   Whittal, Randy M ^b   Li, Liang ^b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHARACTERIZATION; LASER APPLICATIONS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; POLYETHYLENE OXIDES; REACTION KINETICS; SIZE EXCLUSION CHROMATOGRAPHY; SYNTHESIS (CHEMICAL);

CYCLIZATION KINETICS; MATRIX ASSISTED LASER DESORPTION MASS SPECTROSCOPY; PHOSPHORAMIDITES; PYRENE EXCIMER FORMATION; PYRENEBUTANOL;

POLYETHYLENE GLYCOLS;

EID: 0030125776     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma951260h     Document Type: Article

References (51)

1. (a) Semlyen, A., Ed. Cyclic Polymers; Elsevier Applied Science: London, 1986.
2. (b) Winnik, M. A. Chem. Rev. 1981, 81, 491.
3. (a) Cuniberti, C.; Perico, A. Prog. Polym. Sci. 1984, 10, 271.
4. (b) Winnik, M. A. In Molecular Dynamics in Restricted Geometries; Klafter, J., Drake, J. M., Eds.; Wiley: New York, 1989; Chapter 8.
5. (c) Winnik, M. A. In Cyclic Polymers; Semlyen, A., Ed.; Elsevier Applied Science: London, 1986.
6. (a) Cuniberti, C.; Perico, A. Eur. Polym. J. 1977, 13, 369.
7. (b) Winnik, M. A.; Redpath, A. E. C.; Paton, K.; Danhelka, J. Polymer 1984, 25, 91.
8. (a) Winnik, M. A. Acc. Chem. Res. 1985, 18, 73.
9. (b) Boileau, S. B.; Méchin, F.; Martinho, J. M. G.; Winnik, M. A. Macromolecules 1989, 22, 215.
10. (a) Perico, A.; Beggiato, M. Macromolecules 1990, 23, 797.
11. (b) Perico, A.; Altomare, A.; Catalano, D.; Colombani, M.; Veracini, A. A. Macromolecules 1990, 23, 4912.
12. Lee, S.; Winnik, M. A. Can. J. Chem. 1994, 72, 1587.
13. (a) Creel, H. S. Trends Polym. Sci. 1993, 1, 336.
14. (b) Bahr, U.; Deppe, A.; Karas, M.; Hillenkamp, F. Anal. Chem. 1992, 64, 2866.
15. (c) Danis, P. O.; Karr, D. E.; Mayer, F.; Holle, A.; Watson, C. H. Org. Mass Spectrom. 1992, 27, 843.
16. (a) Morton, M. Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983.
17. (b) Young, R. N.; Quirk, R. P.; Fetters, L. J. Adv. Polym. Sci. 1984, 56, 1.
18. (c) Rempp, P.; Franta, E.; Herz, J.-E. Adv. Polym. Sci. 1988, 86, 145.
19. (a) Quirk, R. P.; Perry, S.; Mendicuti, F.; Mattice, W. L. Macromolecules 1988, 21, 2294.
20. (b) Quirk, R. P.; Schock, L. E. Macromolecules 1991, 24, 1237.
21. (c) Quirk, R. P.; Kim, J.; Rodrigues, K.; Mattice, W. L. Makromol. Chem., Macromol. Symp. 1991, 42, 463.
22. (a) Ni, S.; Juhué, D.; Moselhy, J.; Wang, Y.; Winnik, M. A. Macromolecules 1992, 25, 496.
23. (b) Tcherkaaskaya, O.; Ni, S.; Winnik, M. A. Macromolecules, in press.
24. Svirskaya, P.; Danhelka, J.; Redpath, A. E. C.; Winnik, M. A. Polymer 1983, 24, 319.
25. (a) Damha, M. J.; Pon, R. T.; Ogilvie, K. K. Tetrahedron Lett. 1985, 26, 4839.
26. (b) Damha, M. J.; Ogilvie, K. K. J. Org. Chem. 1988, 53, 3710.
27. Lee, S. C.; Winnik, M. A. Manuscript in preparation.
28. (a) Letsinger, R. L.; Finnan, J. L.; Heavner, G. A.; Lunsford, W. B. J. Am. Chem. Soc. 1975, 97, 3278.
29. (b) Letsinger, R. L.; Lunsford, W. B. J. Am. Chem. Soc. 1976, 98, 3655.
30. (c) Beaucage, S. L.; Caruthers, M. H. Tetrahedron Lett. 1981, 22, 1859.
31. (d) McBride, L. J.; Caruthers, M. H. Tetrahedron Lett. 1983, 24, 245.
32. (e) Adams, S. P.; Kavka, K. S.; Wykes, E. J.; Holder, S. B.; Galluppi, G. R. J. Am. Chem. Soc. 1983, 105, 661.
33. (f) Atkinson, T.; Smith, M. In Oligoribonucleotide Synthesis - A Practical Approach; Gait, M. J., Ed.; IRL Press: Oxford, U.K., 1984.
34. (g) Narang, S. A., Ed. Synthesis and Applications of DNA and RNA; Academic Press: New York, 1987.
35. (h) Caruthers, M. H. Acc. Chem. Res. 1991, 24, 278.
36. Moore, M. F.; Beaucage, S. L. J. Org. Chem. 1985, 50, 2019.
37. (a) Tolkmith, H. J. Org. Chem. 1958, 23, 1682.
38. (b) Cremlyn, R. J. W.; Akhtar, N.; Khattak, I. Phosphorus Sulfur 1978, 4, 205.
39. (c) Ogilvie, K. K.; Theriault, N. Y.; Seifert, J.-M.; Pon, R. T.; Nemer, M. J. Can. J. Chem. 1980, 58, 2686.
40. (a) Beaucage, S. L. Tetrahedron Lett. 1984, 25, 375.
41. (b) Koziara, A.; Zwierzak, A. Tetrahedron 1967, 23, 2243.
42. (a) Barone, A. D.; Tang, J.-Y.; Carothers, M. H. Nucleic Acids Res. 1984, 12, 4051.
43. (b) Marugg, J. E.; Bunk, A.; Tromp, M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 2271.
44. (c) Lee, H.-J.; Moon, S.-H. Bull. Chem. Soc. Jpn. 1984, 7, 1229.
45. Inagaki, H.; Matsuda, H.; Kamiyama, F. Macromolecules 1968, 1, 520.
46. Dust, J. M.; Fang, Z.; Harris, J. M. Macromolecules 1990, 23, 3742.
47. Yamakawa, H. Modern Theory of Polymer Solutions; Harper and Row: New York, 1971.
48. Friedman, B.; O'Shaughnesay, B. Macromolecules 1993, 26, 5726.
49. Juhasz, P.; Costello, C. E.; Biemann, K. J. Am. Soc. Mass Spectrosc. 1983, 4, 399.
50. Mattern, D. E.; Hercules, D. M. Anal. Chem. 1985, 57, 2041.
51. Whittal, R. M.; Li, L. Anal. Chem 1995, 67, 1950.