The preparation of new phosphorus-centered functional groups for modified oligonucleotides and other natural phosphates

Molecules

Volumn 10, Issue 9, 2005, Pages 1048-1073

  Gautier, Arnaud ^a,b   Lopin, Chrystel ^a,c   Garipova, Goulnara ^a,e   Dubert, Olivier ^a,d   Kalinina, Irina ^a   Salcedo, Carmen ^a   Balieu, Sébastien ^a   Glatigny, Stéphane ^a   Valnot, Jean Yves ^a   Gouhier, Géraldine ^a   Piettre, Serge R ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c CNRS   (France)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Cyclitol analogue; Difluoro H phosphinates; Difluorophosphonates; Nucleotide analogue; Phosphate isoster

Indexed keywords

CYCLITOL; ION; OLIGONUCLEOTIDE; PHOSPHATE; PHOSPHORUS;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLITOLS; IONS; MODELS, MOLECULAR; OLIGONUCLEOTIDES; PHOSPHATES; PHOSPHORUS;

EID: 33644803161     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10091048     Document Type: Conference Paper

References (138)

1. Hartley, F. R., Ed. The Chemistry of Organophosphorus Compounds, Vol 4, Ter- and Quinquevalent Phosphorus Acids and Their Derivatives; John Wiley & Sons: Chichester, 1996.
2. (a) Blackburn, G. M.; England, D. A.; Kolmann, F. J. Chem. Soc., Chem. Commun. 1981, 930-932;
3. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 1188-1190;
4. (c) McKenna, C. E.; Shen, P.-D. J. Org. Chem. 1981, 46, 4573-4576.
5. (d) Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Perkin Trans 1 1986, 913-917;
6. (e) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763-2764;
7. (f) Burke Jr, T. R.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129-134;
8. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177-184;
9. (h) Higashimoto, Y.; Saito, S.; Tong, X.-H.; Hong, A.; Sakaguchi, K.; Appella, E.; Anderson, C. W. J. Biol. Chem. 2000, 275, 23199-23203.
10. (a) Chambers, R. D.; O'Hagan, D.; Lamont, R. B.; Jain, S. C. Chem. Commun. 1990, 1053-1054;
11. (b) Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272-2281;
12. (c) Nieschalk, J. N.; Batsanov, A. S.; O'Hagan, D.; Chambers, R. D. Tetrahedron 1996, 52, 165-176.
13. (a) Burke Jr., T. R.; Smyth, M. S.; Nomizu, M.; Otaka, A.; Roller, P. P. J. Org. Chem. 1993, 58, 1336-1340;
14. (b) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821-4831;
15. (c) Berkowitz, D. B.; Shen, Q.; Maeng, J.-H. Tetrahedron Lett. 1994, 35, 6445-6448;
16. (d) Burke Jr., T. R.; Ye, B.; Akamatsu, M.; Ford Jr., H.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. J. Med. Chem. 1996, 39, 1021-1027;
17. (e) Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675;
18. (f) Ye, B.; Burke Jr., T. R.; Tetrahedron 1996, 52, 9963-9970;
19. (g) Qabar, M. N.; Urban, J.; Khan, M. Tetrahedron 1997, 53, 11171-11178;
20. (h) Yokomatsu, T.; Abe, H.; Yamagishi, T.; Suemune, K.; Shibuya, S. J. Org. Chem. 1999, 64, 8413-8418;
21. (i) Burke Jr., T. R.; Lee, K. Acc. Chem. Res. 2003, 36, 426-433.
22. (a) Blackburn, G. M.; Kent, D. E. J. Chem. Soc., Chem. Commun. 1981, 511-513;
23. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 1119-1125;
24. (c) Blackburn, G. M.; Guo, M.-J.; Langston, S. P.; Taylor, G. E. Tetrahedron Lett. 1990, 31, 5637-5640;
25. (d) Blackburn, G. M.; S. P. Langston, S. P. Tetrahedron Lett. 1991, 32, 6425-6428;
26. (e) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 55, 3227-3230;
27. (f) Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563-2569;
28. (g) Levvy, S. G.; Wasson, B.; Carson, D. A.; Cottam, H. B. Synthesis 1996, 843-846;
29. (h) Hamilton, C. J.; Roberts, S. M.; Shipitsin, A. J. Chem. Soc., Chem. Comm. 1998, 1087-1088;
30. (i) Hamilton, C. J.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 1051-1056.
31. (a) Collingwood, S. P.; Baxter, A. D. Synlett 1995, 703;
32. (b) Regan, A. C.; Sciammetta, N.; Tattersall, P. I. Tetrahedron Lett. 2000, 41, 8211-8215;
33. (c) Centrone, C. A.; Lowary, T. L. J. Org. Chem. 2003, 68, 8115-8119.
34. For leading references on antisense and antigene strategies, see: (a) De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374;
35. (b) Roush, W. Science 1997, 276, 1192-1193;
36. (c) Gee, J. E.; Robbins, I.; van der Laan, A. C.; van Boom, J. H.; Colombier, C.; Leng, M.; Paible, A. M.; Nelson, J. S.; Lebleu, B. Antisense Nucleic Acid Drug Dev. 1998, 8, 103-111;
37. (d) Crooke, S. T. Biochim. Biophys. Acta 1999, 1489, 31-44;
38. (e) Marcusson, E. G.; Yacyshyn, B. R.; Shanahan, W. R., Jr.; Dean, N. M. Mol Biotechnol. 1999, 12, 1-11;
39. (f) Taylor, J. K.; Dean, N. M. Curr. Opin. Drug Dev. 1999, 2, 147-151;
40. (g) Holmlund, J. T.; Monia, B. P.; Kwoh, T. J.; Dorr, F. A. Curr. Opin. Mol. Ther. 1999, 1, 372-385;
41. (d) Dorr, F. A. Antisense Nucleic Acid Drug Dev. 1999, 9, 391-396;
42. (h) Lebedeva, I. V.; Stein, C. A. BioDrugs 2000, 13, 195-216.
43. For a leading reference on the inositol cycle, see: Billington, D. C. "The Inosiiol Phosphates. Chemical Synthesis and Biological Significance." VCH Publishers : Weinheim, 1991, pp 9-21.
44. (a) McAllister, G.; Whitting, P.; Hammond, E. A.; Knowles, M. R.; Atack, J. R.; Bailey, F. J.; Maigetter, R.; Ragan, C. I. Biochem. J. 1992, 284, 749-754;
45. (b) Bone, R.; Springer, J. P.; Atack, J. R. Proc. Natl. Acad. Sci. USA 1992, 89, 1031-1035;
46. (c) Bone, R.; Frank, L.; Springer, J. P.; Pollack, S. J.; Osborn S.; Atack, J. R.; Knowles, M. R.; McAllister, G.; Ragan, C. I.; Broughton, H. B.; Baker, R.; Fletcher, S. Biochemistry 1994, 33, 9460-9467;
47. (d) Bone, R.; Frank, L.; Springer, J. P.; Atack, J. R. Biochemistry 1994, 33, 9468-9476.
48. (a) Lequeux, T. P.; Percy, J. M. Synlett 1995, 361-362;
49. (b) Piettre, S. R. Tetrahedron Lett. 1996, 37, 2233-2236;
50. (c) Herpin, T. F.; Houlton, J. S.; Motherwell, W. B.; Roberts, B. P.; Weibel, J. M. J. Chem. Soc., Chem. Comm. 1996, 613-614;
51. (d) Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675;
52. (e) Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457-1458;
53. (f) Blades, K.; Cockerill, G. S.; Easterfield, H. J.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1615-1616;
54. (g) Blades, K.; Lapôtre, D.; Percy, J. M. Tetrahedron Lett. 1997, 38, 5895-5898;
55. (h) Herpin, T. F.; Motherwell, W. B.; Roberts, B. P.; Roland, S.; Weibel, J.-M. Tetrahedron 1997, 53, 15085-15100;
56. (i) Blades, K.; Percy, J. M. Tetrahedron Lett. 1998, 39, 9085-9088;
57. (j) Kovensky, J.; McNeil, M.; Sinaÿ, P. J. Org. Chem. 1999, 64, 6202-6205;
58. (k) Butt, A. H.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2000, 1691-1692;
59. (l) Yokomatsu, T.; Katayama, S.; Shibuya, S. Chem. Commun. 2001, 1878-1879;
60. (m) Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. Heterocycles 2002, 56, 273-282;
61. (n) Butt, A. H.; Kariuki, B. M; Percy, J. M.; Spencer, N. S. Chem. Commun. 2002, 682-683;
62. (o) Murano, T.; Muroyama, S.; Yokomatsu, T.; Shibuya, S. Synlett 2002, 1657-1660;
63. (p) Yokomatsu, T.; Kato, J.; Sakuma, C.; Shibuya, S. Synlett 2003, 1407-1410;
64. (q) Murano, T.; Yuasa, Y.; Muroyama, S.; Yokomatsu, T.; Shibuya, S. Tetrahedron 2003, 59, 9059-9073;
65. (r) Murano, T.; Yuasa, Y.; Kobayakawa, H.; Yokomatsu, T.; Shibuya, S. Tetrahedron 2003, 59, 10223-10230.
66. (a) Rees, R. D.; James, K.; Tatchell, A. R.; Williams, R. H. J. Chem. Soc. (C) 1968, 276-2721;
67. (b) Sowa, W. Can. J. Chem. 1968, 46, 1586-1589;
68. (c) Bourgeois, J. M. Helv. Chim. Acta 1975, 53, 363-372;
69. (d) Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69-134;
70. (e) Giese, B.; Gonzàlez-Gomez, J. A.; Witzel, T. Angew. Chem. Chem. Int. Ed. 1984, 23, 69-70;
71. (f) Giese, B. Angew. Chem. Chem. Int. Ed. 1989, 28, 969-980;
72. (g) Schmit, C. Synlett 1994, 241-242;
73. (h) Johnson, C. R.; Bhumralkar, D. R.; De Clercq, E. Nucleosides & Nucleotides 1995, 14, 185-194;
74. (i) Lavaire, S.; Plantier-Royon, R.; Portella, C. J. Carbohydr. Chem. 1996, 15, 361-370;
75. (j) Lavaire, S.; Plantier-Royon, R.; Portella, C. Tetrahedron: Asymmetry 1998, 9, 213-226;
76. (k) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195-10200;
77. (l) Gautier, A.; Garipova, G.; Dubert, O.; Oulyadi, H.; Piettre, S. R. Tetrahedron Lett. 2001, 42, 5673-5676.
78. Lopin, C.; Gouhier, G.; Gautier, A.; Piettre, S. R. J. Org. Chem. 2003, 68, 9916-9923 and references cited therein.
79. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7274;
80. (b) Boeckman, R. K.; Shao, P.; Mullins, J. J. Org. Synth. 2000, 77, 141-152.
81. Serafinowski, P. J.; Barnes, C. L. Synthesis 1997, 225-228.
82. Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. J. Am. Chem. Soc. 2002, 124, 14668-14675.
83. (a) Nifant'ev, E. E.; Koroteev, M.P. Zh. Obshch. Khim. 1967, 37, 1366-1371;
84. (b) Nifant'ev, E. E.; Magdeeva, R. K.; Shchepet'eva, N. P. Zh. Obshch. Khim. 1980, 50, 1416-1422;
85. (c) Nifant'ev, E. E.; Solovetskaya, L. A.; Maslennikova, V. I.; Magdeeva, R. K.; Sergeev, N. M. Zh. Obshch. Khim. 1986, 56, 680-688;
86. (d) Deprele, S.; Montchamps, J.-L. J. Org. Chem. 2001, 66, 6745-6755.
87. Gautier, A.; Garipova, G.; Salcedo, C.; Balieu, S.; Piettre, S. R. Angew. Chem. Int. Ed. 2004, 43. In Press.
88. (a) Stawinski, J.; Kraszewski, A. Acc. Chem. Res. 2002, 55, 952-960;
89. (b) Carruthers, M. H. Acc. Chem. Res. 1991, 24, 278-284;
90. (c) Stawinski, J. "Some Aspects of H-Phosphonate Chemistry"; In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; pp. 377-434.
91. For examples of the Pudovik reaction, see: (a) Pudovik, A. N.; Konovalova, I. V. Zh. Obshch. Khim. 1959, 29, 3342-3346;
92. (b) Pudovik, A. N.; Konovalova, I. V. Zh. Obshch. Khim. 1960, 30, 2348-2352;
93. (c) Pudovik, A. N.; Kusovleva, R. G. Zh. Obshch. Khim. 1965, 55, 354-358;
94. (d) Pudovik, A. N.; Batyeva, E. S. Zh. Obshch. Khim. 1969, 334-337;
95. (e) Semenzin, D.; Etemad-Moghadam, G.; Albouy, D.; Diallo, O.; Koenig, M. J. Org. Chem. 1997, 62, 2414-2422.
96. For examples of the Abramov reaction, see: (a) Abramov, V. S. Dokl. Akad. Nauk S.S.S.R 1950, 75, 487-489;
97. (b) Abramov, V. S.; Semenova L. P; Semenova, L. G. Dokl Akad. Nauk S.S.S.R., 1952; 84, 281-284;
98. (c) Abramov V. S.; Nazmutdinova, A. S. Zh. Obshch. Khim. 1955, 25, 1141-1146;
99. (d) Thiem, J.; Gunther, M.; Paulsen, H.; Kopf, J. Chem. Ber. 1977, 110, 3190-3200;
100. (e) Wroblewski, A. E. Tetrahedron 1986, 42, 3595-3606;
101. (f) Molin, H.; Noren, J. O.; Claesson, A. Carbohydr. Res 1989, 194, 209-221;
102. (g) Engel, R. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992;
103. (h) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976-2985;
104. (i) Hanessian, S.; Galeotti, N.; Rosen, P.; Oliva, G.; Babu, S. Bioorg. Med. Chem. Lett. 1994, 4, 2763-2768;
105. (j) Darrow, J. W.; Drueckhammer, D. G. Bioorg. Med. Chem. 1996, 4, 1341-1348;
106. (k) Harvey, T. C.; Simiand, C.; Weiler, L.; Withers, S. G. J. Org. Chem. 1997, 62, 6722-6725;
107. (l) Hanessian, S.; Rogel, O. Bioorg. Med. Chem. Lett. 1999, 9, 2441-2446;
108. (m) Hanessian, S.; Rogel, O. J. Org. Chem. 2000, 65, 2667-2674.
109. Dubert, O.; Gautier, A.; Condamine, E.; Piettre, S. R. Org. Lett. 2002, 4, 359-362.
110. Waschbüsch, R.; Samadi, M.; Savignac, P. J. Organomet. Chem. 1997, 529, 267-278.
111. Piettre, S. R.; Raboisson, P. Tetrahedron Lett. 1996, 57, 2229-2232.
112. Obayashi, M.; Ito, E.; Kondo, K. Tetrahedron Lett. 1982, 23, 2323-2326.
113. Lopin, C.; Gouhier, G.; Piettre, S. Tetrahedron Lett. 2003, 44. 8837-8840.
114. Nomura, M.; Sato, T.; Washinosu, M.; Tanaka, M.; Asao, T.;Shuto, S.; Matsuda, A. Tetrahedron 2002, 58, 1279-1288.
115. DeLucca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 3041-3043.
116. Kalinina, I.; Gautier, A.; Salcedo, C.; Valnot, J.-Y.; Piettre, S. R. Tetrahedron 2004, 60. 4895-4900.
117. (a) Niedballa, U.; Vorbrüggen, H. Angew. Chem. Int. Ed. 1970, 9, 461-462;
118. (b) Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1974, 39, 3654-3660;
119. (c) ibid, 3660-3663;
120. (d) ibid, 3664-3667;
121. (e) ibid, 3668-3671;
122. (f) ibid, 3672-3674;
123. (g) Niedballa, U.; Vorbrüggen, H. J. Org. Chem. 1976, 41, 2084-2086;
124. (h) Vorbrüggen, H.; Bennua, B. Tetrahedron Lett. 1978, 39, 1339-1342;
125. (i) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255;
126. (j) Vorbrüggen, H.; Hölfe, G. Chem. Ber. 1981, 114, 1256-1268.
127. (a) Saneyoshi, M.; Satoh, E. Chem. Pharm. Bull. 1978, 27, 2518;
128. (b) Zou, R.; Robins, M. J. Can. J. Chem. 1987, 65, 1436-1437;
129. (c) Robins, M. J.; Zou, R.; Guo, Z.; Wnuk, S. F. J. Org. Chem. 1996, 61, 9207-9212.
130. Yokomatsu, T.; Sada, T.; Shimizu, T.; Shibuya, S. Tetrahedron Lett. 1998, 39, 6299-6302.
131. Piettre, S. R. Tetrahedron Lett. 1996, 37, 4707-4710.
132. Kiddle, J. J. Chem. Rev. 1995, 95, 2189-2202.
133. Sabol, J. S.; McCarthy, J. R. Tetrahedron Lett. 1992, 33, 3101-3104.
134. Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 2857-2899.
135. (a) Ferrier, R. J. Chem. Soc., Perkin Trans. 1 1979, 1455-1458;
136. (b) Ferrier, R.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831;
137. (c) Dalko, P.; Sinaÿ, P. Angew. Chem., Int. Ed. 1999, 38, 773-777;
138. (d) Sollogoub, M.; Mallet, J.-M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2000, 39, 362-364.