Pentaerythritol and its congeners: Versatile building blocks for the construction of oligomeric bioconjugates and small molecule libraries on a solid support

Current Organic Chemistry

Volumn 8, Issue 11, 2004, Pages 977-992

  Katajisto, Johanna ^a   Heinonen, Petri ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CELL ENZYME; ESTER; ESTERASE; FUNCTIONAL GROUP; HYDROXYL GROUP; MALONIC ACID DERIVATIVE; OLIGOMER; OLIGONUCLEOTIDE; PENTAERYTHRITOL; PEPTIDE; SPIRO COMPOUND;

ACYLATION; ALDOL REACTION; BIODEGRADATION; CHEMICAL STRUCTURE; COMBINATORIAL LIBRARY; CONJUGATION; CONTROLLED STUDY; DERIVATIZATION; MOLECULAR LIBRARY; MOLECULAR STABILITY; OLIGOMERIZATION; REVIEW; SOLID; SYNTHESIS;

EID: 3042541873     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370258     Document Type: Review

References (86)

1. Blatt, A. H. Org. Synth., Wiley, New York 1955, Collect. Vol. III, p. 476.
2. Herzog, H. Org. Synth., Wiley, New York 1963, Collect. Vol. IV, p. 753.
3. Newkome, G. R.; Arai, S.; Fronczek, F. R.; Moorefield, C. N.; Lim, X.; Weis, C. D. J. Org. Chem., 1993, 58, 898.
4. Litherland, A; Mann, F. G. J. Chem. Soc., 1938, 1588.
5. Wilson, E. R.; Frankel, M. B. J. Org. Chem., 1985, 50, 3211.
6. Anderson, W. S.; Hyer, H. J.; Sundberg, J. E.; Rudy, T. P. Ind. Eng. Chem. Res., 2000, 39, 4011.
7. McAuley, A.; Subramanian, S.; Whitecombe, T. W. Can J. Chem., 1989, 67, 1650.
8. Bruson, H. A. U.S. Patent 2,401,607 (Chem. Abstr. 1946, 40, 5450).
9. Padias, A. B.; Hall, H. K., Jr.; Tomalia, D. A.; McConnell, J. R. J. Org. Chem., 1987, 52, 5305.
10. Newkome, G. R.; Lim, X. Macromolecules, 1991, 24, 1443.
11. Buter, J.; Kellogg, R. M. J. Org. Chem., 1981, 46, 4481.
12. Welck, K. N. J. Chem. Soc., 1930, 257.
13. Block, P., Jr. Org. Synth., 1960, 40, 27.
14. Dekmezian, A. H.; Kaloustian, M. K. Synth. Commun., 1979, 9, 431.
15. Ndibwami, A.; Deslongchamps, P. Can. J. Chem., 1986, 64, 1788.
16. Dubois, J.; Foures, C.; Bory, S.; Falcon, S.; Gaudy, M.; Marquet, A. Tetrahedron, 1991, 47, 1001.
17. Guzaev, A.; Lönnberg, H. Synthesis, 1997, 1281.
18. Newkome, G. R.; Young, J. K.; Baker, G. R.; Potter, R. L.; Audoly, L.; Cooper, D.; Weis, C. D. Macromolecules, 1993, 26, 2394.
19. Kremers, J. A.; Meijer, E. W. J. Org. Chem., 1994, 59, 4262.
20. Kremers, J. A.; Meijer, E. W. React. Funct. Polym., 1995, 26, 137.
21. Halabi, A.; Strumia, M. C. J. Org. Chem., 2000, 65, 9210.
22. Striegler, S. Macromolecules, 2003, 36, 1310.
23. For the DNA-oligomer synthesis, see Iyer, R. P.; Beaucage, S. L. In DNA and Aspects of Molecular Biology; Kool, E. T., Ed.; Pergamon: Amsterdam, 1999, pp. 105-152.
24. For the RNA-oligomer synthesis, see Komatsu, Y.; Ohtsuka, E. In RNA; Söll, D.; Nishimura, S.; Moore, P. B., Eds., Pergamon: Amsterdan, 2001, pp 91-107.
25. Guzaev, A.; Salo, H.; Azhayev, A.; Lönnberg, H. Bioconjugate Chem., 1996, 7, 240.
26. Guzaev, A.; Salo, H.; Azhayev, A.; Lönnberg, H. Tetrahedron, 1995, 51, 9375.
27. Guzaev, A.; Lönnberg, H. Tetrahedron Lett., 1997, 38, 3989.
28. Guzaev, A.; Lönnberg, H. Tetrahedron, 1999, 55, 9101.
29. Shcepinov, M. S.; Udalova, I. A.; Brigman, A. J.; Southern, E. M. Nucleic Acids Res., 1997, 25, 4447.
30. Shcepinov, M. S.; Mir, K. U.; Elder, J. K.; Frank-Kamenetskii, M. D.; Southern, E. M. Nucleic Acids Res., 1999, 27, 3035.
31. Dubber, M.; Fréchet, J. M. J. Bioconjugate Chem., 2003, 14, 239.
32. Hoshika, S.; Ueno, Y.; Matsuda, A. Bioconjugate Chem., 2003, 14, 607.
33. Ueno, Y.; Mikawa, M.; Hoshika, S.; Matsuda, A. Bioconjugate Chem., 2001, 12, 635.
34. Ueno, Y.; Shibata, A.; Matsuda, A.; Kitade, Y. Bioconjugate Chem., 2003, 14, 684.
35. Ueno, Y.; Takeba, M.; Mikawa, M.; Matsuda, A. J. Org. Chem., 1999, 64, 1211.
36. Aojula, H. S.; Offerman, S.; Aojula, R. R.; Hutchinson, A. P.; Nicklin, S.; Clarke, D. J. Biochim. Biophys. Acta, 2002, 1564, 73.
37. Blackburn, G. M.; Beadham, I. G.; Adams, H.; Hutchinson, A. P.; Nicklin, S. J. Chem. Soc. Perkin Trans. 1, 2000, 225.
38. Matsumoto, K.; Davis, B. G.; Jones, J. B. Chem. Eur. J., 2002, 8, 4129.
39. Dyachenko, A. I.; Lukima, M. Y. Izv. Acad Nauk. SSSR, 1966, 2237.
40. Overburger, C. G.; Okamoto, Y.; Bulacovschi, V. Macromoleculaes, 1975, 8, 31.
41. Davis, B. G., Khumtaveeporn, K.; Bott, R. R.; Jones, J. B. Bioorg. Med. Chem., 1999, 7, 2303.
42. Dunn, J. T.; Neumann, W. L.; Rogic, M. M.; Woulfe, S. R. J. Org. Chem., 1990, 55, 6368.
43. Heinonen, P.; Rosenberg, J.; Lönnberg, H. Eur. J. Org. Chem., 2000, 3647.
44. Heinonen, P.; Virta, P.; Lönnberg, H. Tetrahedron, 1999, 55, 7613.
45. For the peptide synthesis by the Boc strategy, see Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W., Wilson, D. Methods Enzymol. 1997, 289, 14.
46. Nudelman, R.; Arden, O.; Hadar, Y.; Chen,Y.; Libman, J.; Shanzer, A. J. Med. Chem., 1998, 41, 1671.
47. Weizman, H.; Ardon, O.; Mester, B.; Libman, J.; Dwir, O.; Hadar, Y.; Chen, Y.; Shanzer, A. J. Am. Chem. Soc., 1996, 118, 12368.
48. Meijler, M. M., Arad-Yellin, R.; Cabantchik, Z. I.; Shanzer, A. J. Am. Chem. Soc., 2002, 124, 12666.
49. Liu, C.-F.; Tam, J. P. Chem. Commun., 1997, 1619.
50. Newkome, G. R.; Lin, X.; Weis, C. D. Tetrahedron: Asymmetry, 1991, 2, 957.
51. Young, J. K.; Baker, G. R.; Newkome, G. R.; Morris, K. F.; Johnson, C. S., Jr. Macromolecules, 1994, 27, 3464.
52. Sadler, K.; Tam, J. P. Rev. Molec. Biotechnol., 2002, 90, 195.
53. Srinivasachar, K.; Neville, D. M., Jr. Biochemistry, 1989, 28, 2501.
54. Virta, P.; Rosenberg, J.; Karskela, T., Heinonen, P.; Lönnberg, H. Eur. J. Org. Chem., 2001, 3467.
55. For the peptide synthesis by the Fmoc strategy, see Wellings, D. A.; Atherton, E. Methods Enzymol., 1997, 289, 44.
56. Virta, P.; Sinkkonen, J.; Lönnberg, H. Eur. J. Org. Chem., 2002, 3616.
57. Bourne, G. T., Meutermans, W. D. F.; Alewood, P. F.; McGeary, R. P.; Scanlon, M.; Watson, A. A.; Smythe, M. L. J. Org. Chem., 1999, 64, 3095.
58. Ranganathan, D.; Samant, M. P.; Karle, I. L. J. Am. Chem. Soc., 2001, 123, 5619.
59. Katajisto, J.; Karskela, T.; Heinonen, P.; Lönnberg, H. J. Org. Chem., 2002, 67, 7995.
60. Karskela, T.; Heinonen, P.; Virta, P.; Lönnberg, H. Eur. J. Org. Chem., 2003, 1687.
61. Lee, Y. C.; Lee, R. T. Acc. Chem. Res., 1995, 28, 321.
62. Whitesides, G. M.; Mammen, M.; Choi, S. Angew. Chem. Int. Ed. Engl., 1998, 37, 2754.
63. Hanessian, S.; Qiu, D., Prabhanjan, H.; Reddy, G. V.; Lou, B. Can. J. Chem., 1996, 74, 1738.
64. Hanessian, S.; Prabhanjan, H.; Qiu, D.; Nambiar, S. Can. J. Chem., 1996, 74, 1731.
65. Hanessian, S.; Hoornaert, C. Carbohydrate Res., 1985, 137, C14.
66. Lindhorst, T. K.; Dubber, M.; Krallmann-Wenzel, U.; Ehlers, S. Eur. J. Org. Chem., 2000, 2027.
67. Langer, P.; Ince, S. J.; Ley, S. V. J. Chem. Soc. Perkin Trans. 1, 1998, 3913.
68. Lehmann, J.; Scheuring, M. Carbohydr. Res., 1995, 276, 57.
69. Lehmann, J.; Weitzel, U. P. Carbohydr. Res., 1996, 294, 65.
70. Veeneman, G. H.; Van Der Hulst, R. G. A.; Van Boeckel, C. A. A.; Philipsen, R. L. A.; Ruigt, G. S. F.; Tonnaer, J. A. D. M.; Van Delft, M. L.; Konings, P. N. M. Bioorg. Med. Chem. Lett., 1995, 5, 9.
71. Liu, B.; Roy, R. Tetrahedron, 2001, 57, 6909.
72. Liu, B.; Roy, R. J. Chem. Soc. Perkin Trans. 1, 2001, 8, 773.
73. Liu, B.; Roy, R. Chem. Commun., 2002, 594.
74. Calvo-Flores, F. G.; Isac-Garcia, J.; Hernández-Mateo, F.; Pérez-Balderas, F.; Calvo-Asin, J. A.; Sanchéz-Vaquero, A.; Santoyo-Gonzáles, F. Org. Lett., 2000, 2, 2499.
75. Hansen, H. C.; Haataja, S.; Finne; J.; Magnusson, G. J. Am. Chem. Soc., 1997, 119, 6974.
76. Hayes, W.; Osborn, H. M. I.; Osborne, S. D.; Rastall, R. A.; Romagnoli, B. Tetrahedron Lett., 2002, 43, 7683.
77. Mikata, Y.; Shinohara, Y.; Yoneda, K.; Nakamura, Y.; Esaki, K.; Tanahashi, M.; Brudzinska, I.; Hirohara, S.; Yokoyama, M.; Mogami, K.; Tanase, T.; Kitayama, T.; Tahashiba, K.; Nabeshima, K.; Takagi, R.; Takatani, M.; Okamoto, T.; Kinoshita, I.; Doe, M.; Hamazawa, A.; Morita, M.; Nishida, F; Sakakibara, Orvig, C.; Yano, S. J. Org. Chem., 2001, 66, 3783.
78. Jayaraman, N.; Stoddart, J. F. Tetrahedron Lett., 1997, 38, 6767.
79. Ashton, P. R.; Boyd, S. E.; Boyd, C. L.; Jayaraman, N.; Stoddart, J. F. Angew. Chem. Int. Ed. Engl., 1997, 36, 732.
80. Hanessian, S.; Prabhanjan, H. Synlett, 1994, 868.
81. Schmidt, M.; Dobner, B.; Nuhn, P. Synlett 2000, 1157.
82. Pátek, M.; Lebl, M. Tetrahedron Lett., 1991, 32, 3891.
83. Farcy, N.; De Muynck, H.; Madder, A.; Hosten, N.; De Clercq, P. J. Org. Lett., 2001, 3, 4299.
84. Poijärvi, P.; Mäki, E.; Tomperi, J.; Ora, M.; Oivanen, M.; Lönnberg, H. Helv. Chim. Acta, 2002, 85, 1869.
85. Poijärvi, P.; Oivanen, M.; Lönnberg, H. Lett. Org. Chem., in press.
86. Ora, M.; Mäki, E.; Poijärvi, P.; Neuvonen, K.; Oivanen, M.; Lönnberg, H. J. Chem. Soc. Perkin Trans. 2, 2001, 6, 881.