Abstract
In this review, a short account of H-phosphonate chemistry and its application to the synthesis of biologically important phosphates and their analogs is given.
References
1. doi:10.1126/science.2434996, F. H. Westheimer. Science 235, 1173 (1987).Search in Google Scholar
2. doi:10.1021/cr00102a001, E. Uhlmann, A. Peyman. Chem. Rev. 90, 543 (1990).Search in Google Scholar
3. C. Helene. Anti-cancer Drug Des. 6, 569 (1991).Search in Google Scholar
4. doi:10.2174/156802606777303658, B. Nawrot, K. Sipa. Curr. Top. Med. Chem. 6, 913 (2006).Search in Google Scholar
5. doi:10.1016/S0968-0896(02)00552-7, C. Schultz. Bioorg. Med. Chem. 11, 885 (2003).Search in Google Scholar
6. D. E. C. Corbridge. Phosphorus. An Outline of Its Chemistry, Biochemistry, and Technology, Elsevier, Amsterdam (1985).Search in Google Scholar
7. E. De Clercq, R. T. Walker (Eds.). Targets for the Design of Antiviral Agents, Plenum Press, New York (1984).10.1007/978-1-4684-4709-5Search in Google Scholar
8. doi:10.1021/ar010049p, J. Stawinski, A. Kraszewski. Acc. Chem. Res. 35, 952 (2002).Search in Google Scholar
9. J. Stawinski. In Handbook of Organophosphorus Chemistry, R. Engel (Ed.), pp. 377-434, Marcel Dekker, New York (1992).Search in Google Scholar
10. J. Stawinski, R. Stromberg. Trends Org. Chem. 4, 31 (1993).Search in Google Scholar
11. A. Kraszewski, J. Stawinski. Trends Org. Chem. 10, 1 (2003).Search in Google Scholar
12. doi:10.1021/ja00209a029, F. H. Westheimer, S. Huang, F. Covitz. J. Am. Chem. Soc. 110, 181 (1988).Search in Google Scholar
13. doi:10.1080/07328318708069994, P. J. Garegg, T. Regberg, J. Stawinski, R. Stromberg. Nucleosides Nucleotides 6, 655 (1987).Search in Google Scholar
14. I. Y. Dubey, V. A. Efimov, T. V. Lyapina, D. M. Fedoryak. Bioorg. Khim. 18, 911 (1992).Search in Google Scholar
15. doi:10.1021/cr00029a008, D. G. Gilheany. Chem. Rev. 94, 1339 (1994).Search in Google Scholar
16. doi:10.1021/cr60212a003, A. W. Frank. Chem. Rev. 61, 389 (1961).Search in Google Scholar
17. R. Stromberg, J. Stawinski. Nucleic Acids Symp. Ser. 18, 185 (1987).Search in Google Scholar
18. doi:10.1021/ja9726015, T. Wada, Y. Sato, F. Honda, S. Kawahara, M. Sekine. J. Am. Chem. Soc. 119, 12710 (1997).Search in Google Scholar
19. doi:10.1093/nar/21.23.5337, V. A. Efimov, A. L. Kalinkina, O. G. Chakhmakhcheva. Nucleic Acids Res. 21, 5337 (1993).Search in Google Scholar
20. doi:10.1016/S0040-4020(01)93865-7, M. Mikolajczyk, J. Luczak. Tetrahedron 28, 5411 (1972).Search in Google Scholar
21. doi:10.1021/ja01015a030, T. L. Emmick, R. L. Letsinger. J. Am. Chem. Soc. 90, 3459 (1968).Search in Google Scholar
22. doi:10.1080/07328319108046511, J. Stawinski, R. Stromberg, M. Thelin. Nucleosides Nucleotides 10, 511 (1991).Search in Google Scholar
23. doi:10.1021/jo00049a022, H. Almer, J. Stawinski, R. Stromberg, M. Thelin. J. Org. Chem. 57, 6163 (1992).Search in Google Scholar
24. doi:10.1039/c39900001154, F. Seela, U. Kretschmer. J. Chem. Soc., Chem. Commun. 1154 (1990).Search in Google Scholar
25. doi:10.1021/jo00012a017, F. Seela, U. Kretschmer. J. Org. Chem. 56, 3861 (1991).Search in Google Scholar
26. doi:10.1080/07328319108046582, C. Battistini, M. G. Brasca, S. Fustioni. Nucleosides Nucleotides 10, 723 (1991).Search in Google Scholar
27. doi:10.1016/S0968-0896(01)00140-7, T. Johansson, J. Stawinski. Bioorg. Med. Chem. 9, 2315 (2001).Search in Google Scholar
28. doi:10.1093/nar/14.13.5399, B. C. Froehler, P. G. Ng, M. D. Matteucci. Nucleic Acids Res. 14, 5399 (1986).Search in Google Scholar
29. doi:10.1016/S0040-4039(00)97293-9, S. Agrawal, J.-Y. Tang. Tetrahedron Lett. 31, 7541 (1990).Search in Google Scholar
30. doi:10.1021/jo00017a033, J. Stawinski, M. Thelin. J. Org. Chem. 56, 5169 (1991).Search in Google Scholar
31. doi:10.1021/jo980491u, J. Jankowska, A. Sobkowska, J. Cieslak, M. Sobkowski, A. Kraszewski, J. Stawinski, D. Shugar. J. Org. Chem. 63, 8150 (1998).Search in Google Scholar
32. doi:10.1021/jo00267a020, I. Lindh, J. Stawinski. J. Org. Chem. 54, 1338 (1989).Search in Google Scholar
33. doi:10.1021/jo00080a021, J. Stawinski, M. Thelin. J. Org. Chem. 59, 130 (1994).Search in Google Scholar
34. doi:10.1016/S0040-4039(00)85269-7, B. C. Froehler. Tetrahedron Lett. 27, 5575 (1986).Search in Google Scholar
35. doi:10.1073/pnas.86.17.6553, R. L. Letsinger, G. Zhang, D. K. Sun, T. Ikeuchi, P. S. Sarin. Proc. Natl. Acad. Sci. USA 86, 6553 (1989).Search in Google Scholar
36. J. Stawinski, R. Stromberg. In Current Protocols in Nucleic Acid Chemistry, S. L. Beaucage, D. E. Bergstrom, G. D. Glick, R. A. Jones (Eds.), pp. 2.6.1-2.6.15, John Wiley, New York (2001).Search in Google Scholar
37. P. J. Garegg, T. Regberg, J. Stawinski, R. Stromberg. Chem. Scr. 26, 59 (1986).Search in Google Scholar
38. doi:10.1016/S0040-4039(00)84506-2, J. E. Marugg, A. Burik, M. Tromp, G. A. van der Marel, J. H. van Boom. Tetrahedron Lett. 27, 2271 (1986).Search in Google Scholar
39. doi:10.1080/07328319008045116, J. Stawinski, M. Thelin. Nucleosides Nucleotides 9, 129 (1990).Search in Google Scholar
40. doi:10.1016/S0040-4039(00)76906-1, J. Jankowska, M. Sobkowski, J. Stawinski, A. Kraszewski. Tetrahedron Lett. 35, 3355 (1994).Search in Google Scholar
41. doi:10.1021/jo00298a023, J. Stawinski, M. Thelin, E. Westman, R. Zain. J. Org. Chem. 55, 3503 (1990).Search in Google Scholar
42. doi:10.1016/S0040-4039(01)02182-7, M. Bollmark, M. Kullberg, J. Stawinski. Tetrahedron Lett. 43, 515 (2002).Search in Google Scholar
43. doi:10.1016/S0040-4039(97)00218-9, J. Jankowska, J. Cieslak, A. Kraszewski, J. Stawinski. Tetrahedron Lett. 38, 2007 (1997).Search in Google Scholar
44. doi:10.1021/ja00110a002, P. H. Seeberger, E. Yau, M. H. Caruthers. J. Am. Chem. Soc. 117, 1472 (1995).Search in Google Scholar
45. doi:10.1002/ejoc.200400550, G. Laven, J. Nilsson, J. Stawinski. Eur. J. Org. Chem. 5111 (2004).Search in Google Scholar
46. M. Kullberg, J. Stawinski. Synthesis 1668 (2005).10.1055/s-2005-865300Search in Google Scholar
47. doi:10.1016/S0040-4039(01)80782-6, G. M. Porritt, C. B. Reese. Tetrahedron Lett. 30, 4713 (1989).Search in Google Scholar
48. J. Stawinski, T. Szabo, M. Thelin, E. Westman, R. Zain. Collect. Czech. Chem. Commun. 55, 141 (1990).10.1135/cccc1990s141Search in Google Scholar
49. doi:10.1021/jo000729q, J. Cieslak, J. Jankowska, J. Stawinski, A. Kraszewski. J. Org. Chem. 65, 7049 (2000).Search in Google Scholar
50. doi:10.1080/15257779508012455, J. Stawinski, R. Zain. Nucleosides Nucleotides 14, 711 (1995).Search in Google Scholar
51. doi:10.1039/p29960000795, R. Zain, J. Stawinski. J. Chem. Soc., Perkin Trans. 2 795 (1996).Search in Google Scholar
52. doi:10.1021/jo960810m, R. Zain, J. Stawinski. J. Org. Chem. 61, 6617 (1996).Search in Google Scholar
53. doi:10.1135/cccc20060820, M. Kullberg, M. Bollmark, J. Stawinski. Collect. Czech. Chem. Commun. 71, 820 (2006).Search in Google Scholar
54. doi:10.1039/b000727g, D. V. Yashunsky, A. V. Nikolaev. J. Chem. Soc., Perkin Trans. 1 8, 1195 (2000).Search in Google Scholar
55. doi:10.1016/j.carres.2006.10.006, A. V. Nikolaev, I. V. Botvinko, A. J. Ross. Carbohydr. Res. 342, 297 (2007).Search in Google Scholar
56. doi:10.1021/jo962224z, A. Sobkowska, M. Sobkowski, J. Cieslak, A. Kraszewski, I. Kers, J. Stawinski. J. Org. Chem. 62, 4791 (1997).Search in Google Scholar
57. doi:10.1021/jo00186a012, A. Kume, M. Fujii, M. Sekine, T. Hata. J. Org. Chem. 49, 2139 (1984).Search in Google Scholar
58. doi:10.1016/S0040-4020(01)81543-X, S. L. Beaucage, R. P. Iyer. Tetrahedron 49, 10441 (1993).Search in Google Scholar
59. doi:10.1039/jr9520003669, N. S. Corby, G. W. Kenner, A. R. Todd. J. Chem. Soc. 3669 (1952).Search in Google Scholar
60. doi:10.1016/S0040-4039(00)84909-6, P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Stromberg, C. Henrichson. Tetrahedron Lett. 27, 4055 (1986).Search in Google Scholar
61. doi:10.1016/S0040-4039(00)84908-4, P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Stromberg, C. Henrichson. Tetrahedron Lett. 27, 4051 (1986).Search in Google Scholar
62. doi:10.1016/S0040-4039(00)85507-0, B. C. Froehler, M. D. Matteucci. Tetrahedron Lett. 27, 469 (1986).Search in Google Scholar
63. doi:10.1039/p19870001269, P. J. Garegg, T. Regberg, J. Stawinski, R. Stromberg. J. Chem. Soc. Perkin Trans. 1 1269 (1987).Search in Google Scholar
64. doi:10.1016/S0040-4039(00)60887-0, J. Stawinski, M. Thelin. Tetrahedron Lett. 33, 7255 (1992).Search in Google Scholar
65. doi:10.1016/S0040-4039(00)79848-0, J. Stawinski, M. Thelin. Tetrahedron Lett. 33, 3189 (1992).Search in Google Scholar
66. doi:10.1039/jr9470000674, R. F. Atherton, A. R. Todd. J. Chem. Soc. 674 (1947).Search in Google Scholar
67. doi:10.1080/07328319608002390, A. Kers, I. Kers, A. Kraszewski, M. Sobkowski, T. Szabo, M. Thelin, R. Zain, J. Stawinski. Nucleosides Nucleotides 15, 361 (1996).Search in Google Scholar
68. doi:10.1080/07328319808005208, M. Bollmark, J. Stawinski. Nucleosides Nucleotides 17, 663 (1998).Search in Google Scholar
69. R. Stromberg, J. Stawinski. In Current Protocols in Nucleic Acid Chemistry, S. L. Beaucage, D.E. Bergstrom, G. D. Glick, R. A. Jones (Eds.), pp. 3.4.1-3.4.11, Suppl. 19, John Wiley, New York (2004).Search in Google Scholar
70. doi:10.1016/S0040-4039(98)01513-5, T. Wada, A. Mochizuki, Y. Sato, M. Sekine. Tetrahedron Lett. 39, 7123 (1998).Search in Google Scholar
71. doi:10.1021/ja00830a039, T. Hata, M. Sekine. J. Am. Chem. Soc. 96, 7363 (1974).Search in Google Scholar
72. doi:10.1081/NCN-100002335, J. Lin, B. R. Shaw. Nucleosides Nucleotides 20, 587 (2001).Search in Google Scholar
73. E. de Vroom, M. L. Spierenburg, C. E. Dreef, G. A. van der Marel, J. H. van Boom. Recl. Trav. Chim. Pays-Bas 106, 65 (1987).10.1002/recl.19871060206Search in Google Scholar
74. doi:10.1016/S0040-4020(97)00790-4, A. Kers, J. Stawinski, L. Dembkowski, A. Kraszewski. Tetrahedron 53, 12691 (1997).Search in Google Scholar
75. doi:10.1021/cr60307a003, R. Engel. Chem. Rev. 77, 349 (1977).Search in Google Scholar
76. C. Thibaudeau, P. Acharya, J. Chattopadhyaya. Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications, Uppsala University, Uppsala (2005).Search in Google Scholar
77. doi:10.1016/S0040-4039(99)00702-9, A. Kers, J. Stawinski. Tetrahedron Lett. 40, 4263 (1999).Search in Google Scholar
78. doi:10.1016/S0040-4039(01)00115-0, T. Johansson, A. Kers, J. Stawinski. Tetrahedron Lett. 42, 2217 (2001).Search in Google Scholar
79. doi:10.1016/j.tet.2003.11.010, T. Johansson, J. Stawinski. Tetrahedron 60, 389 (2004).Search in Google Scholar
80. doi:10.1055/s-1981-29335, T. Hirao, T. Masunaga, Y. Ohshiro, T. Agawa. Synthesis 56 (1981).Search in Google Scholar
81. doi:10.1039/b108857m, T. Johansson, J. Stawinski. Chem. Commun. 2564 (2001).Search in Google Scholar
82. G. Laven, J. Stawinski. Collect. Symp. Ser. 7, 195 (2005).Search in Google Scholar
83. doi:10.1039/b305689a, K. Zmudzka, T. Johansson, M. Wojcik, M. Janicka, M. Nowak, J. Stawinski, B. Nawrot. New J. Chem. 27, 1698 (2003).Search in Google Scholar
84. doi:10.1080/10426509108029443, P. Kafarski, B. Lejczak. Phosphorus Sulfur Silicon 63, 193 (1991).Search in Google Scholar
85. doi:10.1002/1098-1071(2000)11:7<480::AID-HC6>3.0.CO;2-J, J. M. Huang, R. Y. Chen. Heteroat. Chem. 11, 480 (2000).Search in Google Scholar
86. doi:10.1016/S0022-328X(97)00176-9, S. R. Davies, M. C. Mitchell, C. P. Cain, P. G. Devitt, R. J. Taylor, T. P. Kee. J. Organometal. Chem. 550, 29 (1998).Search in Google Scholar
87. O. I. Kolodiazhnyi. Usp. Khim. 75, 254 (2006).10.1070/RC2006v075n03ABEH001193Search in Google Scholar
88. doi:10.1016/j.bmc.2005.10.048, A. Szymanska, M. Szymczak, J. Boryski, J. Stawinski, A. Kraszewski, G. Collu, G. Sanna, G.Giliberti, R. Loddo, P. La Colla. Bioorg. Med. Chem. 14, 1924 (2006).Search in Google Scholar
89. doi:10.1080/10426509208049167, J. Vepsalainen, E. Pohjala, H. Nupponen, P. Vainiotalo, M. Ahlgren. Phosphorus Sulfur Silicon 70, 183 (1992).Search in Google Scholar
90. doi:10.1007/3-540-45731-3_8, C. E. McKenna, B. A. Kashemirov. In New Aspects in Phosphorus Chemistry, J. P. Majoral (Ed.), pp. 201-238 (2002).Search in Google Scholar
91. doi:10.1021/ol035166u, M. Szymczak, A. Szymanska, J. Stawinski, J. Boryski, A. Kraszewski. Org. Lett. 5, 3571 (2003).Search in Google Scholar
92. doi:10.1021/jm00391a027, L. M. Nguyen, E. Niesor, C. L. Bentzen. J. Med. Chem. 30, 1426 (1987).Search in Google Scholar
93. doi:10.1080/10426500008045216, I. Mallard, J. M. Benech, M. Lecouvey, Y. Leroux. Phosphorus Sulfur Silicon 162, 15 (2000).Search in Google Scholar
94. M. Kullberg, J. Stawinski. Collect. Symp. Ser. 7, 207 (2005).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston