Synthesis and properties of carbohydrate - Phosphate backbone - Modified oligonucleotide analogues and nucleic acid mimetics

Russian Chemical Reviews

Volumn 80, Issue 5, 2011, Pages 429-452

  Abramova, T V ^a   Silnikov, V N ^a  

^a INSTITUTE OF CHEMICAL BIOLOGY AND FUNDAMENTAL MEDICINE   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79959611514     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2011v080n05ABEH004188     Document Type: Review

References (285)

1. V Holoubek, L Fanshier, T T Crocher Exp. Cell Res. 44 362 (1962).
2. M C Niu, L C Niu, A Guha Proc. Soc. Exp. Biol. Med. 128 550 (1968).
3. C B Reese Org. Biomol. Chem. 3 3851 (2005).
4. J Pitha, P M Pitha, E Stuart Biochemistry 10 4595 (1971).
5. M G Boulton, A S Jones, R T Walker Biochim. Biophys. Acta 246 197 (1971).
6. G J Couling, A S Jones, R T Walker Biochim. Biophys. Acta 254 452 (1971).
7. A S Jones Int. J. Biol. Macromol. 1 194 (1979).
8. B S Sproat J. Biotechnol. 41 221 (1995).
9. C Hél̀ene, J-J Toulmé Biochim. Biophys. Acta 1049 99 (1990).
10. R V Giles, D G Spiller, J A Green, R E Clark, D M Tidd Blood 86 744 (1995).
11. M Koziolkiewicz, A Wilk, in Protocols for Oligonucleotides and Analogues. Synthesis and Properties. Methods in Molecular Biology Vol. 20 (Ed. S Agrawal) (Totowa, NJ: Humana Press, 1993) p. 207.
12. P S Miller, C D Cushman, J T Levi, in Oligonucleotides and Analogues. A Practical Approach (The Practical Approach Series) (Ed. F Eckstein) (New York: Oxford University Press, 1991) p. 137.
13. R F Schinazi, Z J Lesnikowski Nucleosides Nucleotides 17 635 (1998).
14. G Zon, in Protocols for Oligonucleotides and Analogues. Synthesis and Properties. Methods in Molecular Biology Vol. 20 (Ed. S Agrawal) (Totowa, NJ: Humana Press, 1993) p. 165.
15. B S Sproat, A I Lamond, in Oligonucleotides and Analogues. A Practical Approach (The Practical Approach Series) (Ed. F Eckstein) (New York: Oxford University Press, 1991) p. 49.
16. R I Hogrefe Antisense Nucleic Acid Drug Dev. 9 351 (1999).
17. Antisense Research and Applications (Eds S T Crooke, B Lebleu) (Boca Raton, FL: CRC Press, 1993).
18. S I Antsypovitch Usp. Khim. 71 81 (2002).
19. [Russ. Chem. Rev. 71 71 (2002)].
20. J Summerton, D Weller Antisense Nucleic Acid Drug Dev. 7 187 (1997).
21. J Summerton Biochim. Biophys. Acta 1489 141 (1999).
22. S M Gryaznov Biochim. Biophys. Acta 1489 131 (1999).
23. M Petersen, J Wengel Trends Biotechnol. 21 74 (2003).
24. J Micklefield Curr. Med. Chem. 8 1157 (2001).
25. J Kurreck Eur. J. Biochem. 270 1628 (2003).
26. A V Aershot Antiviral Res. 71 307 (2006).
27. D A Braasch, D R Corey Biochemistry 41 4504 (2002).
28. E R Rayburn, R Zhang Drug Discov. Today 13 513 (2008).
29. R Juliano, J Bauman, H Kang, X Ming Mol. Pharmacol. 6 686 (2009).
30. Antisense Drug Technology: Principles, Strategies, and Applications (2nd Ed.) (Ed. S T Crooke) (Boca Raton, FL: CRC Press, 2008).
31. N Venkatesan, B H Kim Chem. Rev. 106 3712 (2006).
32. H Llnnberg Bioconjugate Chem. 20 1065 (2009).
33. A Gissot, M Campo, M W Grinstaff, P Barth́lémy Org. Biomol. Chem. 6 1324 (2008).
34. G De Rosa, M I La Rotonda Molecules 14 2801 (2009).
35. C B Reese, H Yan J. Chem. Soc., Perkin Trans. 1 2619 (2002).
36. Z S Cheruvalleth, R L Carty, M N Moore, D C Capaldi, A H Krotz, P D Wheeler, B J Turney, S R Craig, H J Gaus, A N Scozzary, D L Cole, V T Ravikumar Org. Process Res. Dev. 4 199 (2000).
37. J-Y Tang, Y Han, J X Tang, Z Zhang Org. Process Res. Dev. 4 194 (2000).
38. Q Song, Z Wang, Y S Sanghivi Nucleosides, Nucleotides Nucleic Acids 22 629 (2003).
39. V T Ravikumar, R K Kumar, D C Capaldi, D L Cole Nucleosides, Nucleotides Nucleic Acids 22 1421 (2003).
40. Z Wang, P Olsen, V T Ravikumar Nucleosides, Nucleotides Nucleic Acids 26 259 (2007).
41. W J Stec, Z J Lesnikovwski, in Protocols for Oligonucleotides and Analogues. Synthesis and Properties. Methods in Molecular Biology Vol. 20 (Ed. S Agrawal) (Totowa, NJ: Humana Press, 1993) p. 285.
42. H Almer, T Szabo, J Stawinski Chem. Commun. 290 (2004).
43. V A Efimov, A A Buryakova, I Y Dubey, N N Polushin, O G Chakhmakhcheva, Yu A Ovchinnikov Nucleic Acids Res. 13 6525 (1986).
44. V A Efimov, N S Molchanova, O G Chakhmakhcheva Nucleosides, Nucleotides Nucleic Acids 26 1087 (2007).
45. Y Lu Mini-Rev. Med. Chem. 6 319 (2008).
46. L Cummins, D Graff, G Beaton, W S Marshall, M H Caruthers Biochemistry 35 8734 (1996).
47. M Olesiak, W J Stec, A Okruszek Org. Biomol. Chem. 7 2162 (2009).
48. F Eckstein Annu. Rev. Biochem. 54 367 (1985).
49. B R Shaw, J Madison, A Sood, B F Spielvogel, in Protocols for Oligonucleotides and Analogues. Synthesis and Properties. Methods in Molecular Biology Vol. 20 (Ed. S Agrawal) (Totowa, NJ: Humana Press, 1993) p. 225.
50. P Li, Z A Sergueeva, M Dobrikov, B R Shaw Chem. Rev. 107 4746 (2007).
51. T Wada, M Shimizu, N Oka, K Saigo Nucleosides, Nucleotides Nucleic Acids 22 1171 (2003).
52. M Shimizu, T Wada, N Oka, K Saigo J. Org. Chem. 69 5261 (2004).
53. M Shimizu, K Saigo, T Wada J. Org. Chem. 71 4262 (2006).
54. Y Enya, S Nagata, Y Masutomi, H Kitagawa, K Takagaki, N Oka, T Wada, T Ohgi, J Yano Bioorg. Med. Chem. 16 9154 (2008).
55. T Kawanaka, M Shimizu, N Shintani, T Wada Bioorg. Med. Chem. Lett. 18 3783 (2008).
56. T Wada, Y Maizuru, M Shimizu, N Oka, K Saigo Bioorg. Med. Chem. Lett. 16 3111 (2006).
57. N Iwamoto, N Oka, T Wada Nucleic Acids Symp. Ser. 53 9 (2009).
58. T J Matray, S M Gryaznov Nucleic Acids Res. 27 3976 (1999).
59. B-S Herbert, K Pongracz, J W Shay, S M Gryaznov Oncogene 21 638 (2002).
60. K Pongracz, S Li, B-S Herbert, R Pruzan, E Wunder, A Chin, M Piatyszek, J Shay, S M Gryaznov Nucleosides, Nucleotides Nucleic Acids 22 1627 (2003).
61. S M Gryaznov Chem. Biodiv. 7 477 (2010).
62. V A Efimov, M V Choob, A L Kalinkina, O G Chakhmakhcheva Nucleosides Nucleotides 16 1475 (1997).
63. D Rejman, M Masojíková, I Rosenberg Nucleosides, Nucleotides Nucleic Acids 23 1683 (2004).
64. H An, T Wang, M A Maier, M Manoharan, B S Ross, P D Cook J. Org. Chem. 66 2789 (2001).
65. Š Králíkova, M Masojíkova, M Buděšínský, I Rosenberg Nucleosides, Nucleotides Nucleic Acids 22 329 (2003).
66. Š Králíkova,I Buděšínský , I Rosenberg Nucleosides, Nucleotides Nucleic Acids 22 1061 (2003).
67. Z Točík, I Bravík Jr, M Buděší nskýI Rosenberg Biopolymers 83 400 (2006).
68. Z Točik, M Buděšínsky, I Bravík Jr, I Rosenberg Nucleic Acids Symp. Ser. 52 427 (2008).
69. O Páv, M Buděšínský, I Rosenberg Nucleosides, Nucleotides Nucleic Acids 22 1053 (2003).
70. M Petrová, Š Králíkova, M Buděšínský, I Rosenberg Nucleic Acids Symp. Ser. 52 591 (2008).
71. I Kóšiová, I Rosenberg Nucleic Acids Symp. Ser. 52 569 (2008).
72. R Liboska, M Petrová, R Pohl, M Buděší nský, V Hurychová, I Rosenberg Nucleic Acids Symp. Ser. 52 317 (2008).
73. R M Crooke, n Antisense Research and Applications (Eds S T Crooke, B Lebleu) (Boca Raton, FL: CRC Press, 1993) p. 427.
74. M Prhavc, B Bhat, G Just, P D Cook, M Manoharan Nucleosides, Nucleotides Nucleic Acids 20 995 (2001).
75. X Yang, X Han, C Cross, S Bare, Y Sanghvi, X Gao Biochemistry 38 12586 (1999).
76. J Micklefield, K J Fettes Tetrahedron 54 2129 (1998).
77. K J Fettes, N Howard, D T Hickman, S A Adah, M R Player, P F Torrence, J Micklefield Chem. Commun. 765 (2000).
78. K J Fettes, N Howard, D T Hickman, S Adah, M R Player, P F Torrence, J Micklefield J. Chem. Soc., Perkin Trans. 1 485 (2002).
79. N J Caplen Gene Ther. 11 1241 (2004).
80. A DeMesmaeker, A Waldner, J Lebreton, V Fritsch, R M Wolf, in Carbohydrate Modifications in Antisense Research (ACS Symp. Ser.) Vol. 580 (Eds Y S Sanghvi, P D Cook) (Washington, DC: American Chemical Society, 1994) p. 24.
81. M A Peterson, B L Nilsson, S Sarker, B Doboszewski, W Zhang, M J Robins J. Org. Chem. 65 8183 (1999).
82. S V Kochetkova, A M Varizhuk, N A Kolganova, E N Timofeev, V L Florent'ev Bioorg. Khim. 35 76 (2009) a.
83. S V Kochetkova, A M Varizhuk, N A Kolganova, E N Timofeev, V L Florent'ev Bioorg. Khim. 35 202 (2009) a.
84. A M Varizhuk, S V Kochetkova, N A Kolganova, E N Timofeev, V L Florent'ev Bioorg. Khim. 35 650 (2009) a.
85. E Rozners, Y Liu J. Org. Chem. 70 9841 (2005).
86. R Threlfall, A Devies, N M Howarth, J Fisher, R Cosstick Chem. Commun. 585 (2008).
87. J B Epp, T S Widlanski J. Org. Chem. 64 293 (1999).
88. V A Kumar, K N Ganesh Curr. Top. Med. Chem. 7 715 (2007).
89. V A Efimov, A A Buryakova, O G Chakhmakhcheva Bioorg. Med. Chem. Lett. 8 1013 (1998).
90. S V Kochetkova, N A Kolganova, E N Timofeev, V L Florent'ev Bioorg. Khim. 34 506 (2008) a.
91. S V Kochetkova, E A Fillipova, N A Kolganova, E N Timofeev, V L Florent'ev Bioorg. Khim. 34 227 (2008) a.
92. K Gogoi, A D Gunjal, V A Kumar Chem. Commun. 2373 (2006).
93. K Gogoi, A D Gunjal, U D Phalgune, V A Kumar Org. Lett. 9 2697 (2007).
94. S Gokhale, V A Kumar Nucleic Acids Symp. Ser. 52 145 (2008).
95. H Kaur, A Arora, K Gogoi, P Solanke, A D Gunjal, V A Kumar J. Phys. Chem. B 113 2944 (2009).
96. K Gogoi, V A Kumar Chem. Commun. 706 (2008).
97. S Bagmare, M D'Costa, V A Kumar Chem. Commun. 6646 (2009).
98. P S Pallan, P von Matt, C J Wilds, K-H Altmann, M Egli Biochemistry 45 8048 (2006).
99. F Debart, S Abes, G Deglane, H M Moulton, P Clair, M J Gait, J-J Vasser, B Lebleu Curr. Top. Med. Chem. 7 727 (2007).
100. S V Kochetkova, E N Timofeev, E A Korobeinikova, N A Kolganova, V L Florentiev Tetrahedron 57 10287 (2001).
101. R O Dempcy, Ö Almarsson, T C Bruice Proc. Natl. Acad. Sci. USA 91 7864 (1994).
102. D A Barawkar, T C Bruice Proc. Natl. Acad. Sci. USA 95 11047 (1998).
103. B A Linkletter, T C Bruice Bioorg. Med. Chem. 8 1893 (2000).
104. P M Reddy, T C Bruice Bioorg. Med. Chem. Lett. 13 1281 (2003).
105. H Challa, T C Bruice Bioorg. Med. Chem. 12 1475 (2004).
106. I E Szabo, T C Bruice Bioorg. Med. Chem. 12 4233 (2004).
107. J W Toporowski, S Y Reddy, T C Bruice Bioorg. Med. Chem. 13 3691 (2005).
108. M L Jain, T C Bruice Bioorg. Med. Chem. 14 7333 (2006).
109. J W Toporowski, S Y Reddy, T C Bruice Biophys. Chem. 126 132 (2007).
110. C Richert, A L Roughton, S A Benner J. Am. Chem. Soc. 118 4518 (1996).
111. Z Huang, S A Benner J. Org. Chem. 67 3996 (2002).
112. D Sheehan, B Lunstad, C M Yamada, B G Stell, M H Caruthers, D J Deliger Nucleic Acids Res. 31 4109 (2003).
113. C M Yamada, D J Delinger, M H Caruthers J. Am. Chem. Soc. 128 5251 (2006).
114. E Rozners, D Katkevica, R Strömberg ChemBioChem 8 537 (2007).
115. A Kolarovic, E Schweizer, E Greene, M Gironda, P S Pallan, M Egli, E Rozners J. Am. Chem. Soc. 131 14932 (2009).
116. N M Bell, J Micklefield ChemBioChem 10 2691 (2009).
117. M Egli, P S Pallan Annu. Rev. Biophys. Biomol. Struct. 36 281 (2007).
118. T S Zatsepin, E A Romanova, T S Oretskaya Usp. Khim. 71 586 (2002).
119. [Russ. Chem. Rev. 71 513 (2002)].
120. T S Zatsepin, E A Romanova, T S Oretskaya Usp. Khim. 73 757 (2004).
121. [Russ. Chem. Rev. 73 701 (2004)].
122. A A Koshkin, S K Singh, P Nielsen, V K Rajwanshi, R Kumar, M Meldgaard, C E Olsen, J Wengel Tetrahedron 54 3607 (1998).
123. T P Prakash, A M Kawasaki, E V Wancewicz, L Shen, B P Monia, B S Ross, B Bhat, M Manoharan J. Med. Chem. 51 2766 (2008).
124. T P Prakash, M Manoharan, A M Kawasaki, A S Fraser, E A Lesnik, N Sioufi, J M Leeds, M Teplova, M Egli Biochemistry 41 11642 (2002).
125. M Prhavc, T P Prakash, G Minasov, P D Cook, M Egli, M Manoharan Org. Lett. 5 2017 (2003).
126. M Prhavc, E A Lesnik, V Mohan, M Manoharan Tetrahedron Lett. 42 8777 (2001).
127. T P Prakash, A M Kawasaki, E A Lesnik, S R Owens, M Manoharan Org. Lett. 5 403 (2003).
128. R Pattanayek, L Sethaphong, C Pan, M Prhavc, T P Prakash, M Manoharan, M Egli J. Am. Chem. Soc. 126 15006 (2004).
129. M Egli, G Minasov, V Tereshko, P S Pallan, M Teplova, G B Inamati, EALesnik, SROwens, B S Ross, T P Prakash, M Manoharan Biochemistry 44 9045 (2005).
130. P S Pallan, M Egli Nat. Protoc. 2 647 (2007).
131. T P Prakash, M Manoharan, A S Fraser, A M Kawasaki, E A Lesnik, S R Owens Tetrahedron Lett. 41 4855 (2000).
132. T P Prakash, A Püschl, E Lesnik, V Mohan, V Tereshko, M Egli, M Manoharan Org. Lett. 6 1971 (2004).
133. T P Prakash, B Bhat Curr. Top. Med. Chem. 7 641 (2007).
134. T S Zatsepin, E A Romanova, D A Stetsenko, M J Gait, T S Oretskaya Nucleosides, Nucleotides Nucleic Acids 22 1383 (2003).
135. P E Burmeister, C Wang, J R Killough, S D Lewis, L R Horwitz, A Ferguson, K M Thomson, P S Pendergrast, T G McCauley, M Kurz, J Diener, S T Cload, C Wilson, A D Keefe Oligonucleotides 16 337 (2006).
136. N C Seeman Trends Biochem. Sci. 30 119 (2005).
137. N C Seeman Chem. Biol. 10 1151 (2003).
138. L Zhu, P S Lukeman, J W Canary, N C Seeman J. Am. Chem. Soc. 125 10178 (2003).
139. Y Liu, R Wang, L Ding, R Sha, P S Lukeman, J W Canary, N C Seeman ChemBioChem 9 1641 (2008).
140. D A Braasch, D R Corey Chem. Biol. 8 1 (2001).
141. K Bondensgaard, M Petersen, S K Singh, V K Rajwanshi, R Kumar, J Wengel, J P Jacobsen Chem. - Eur. J. 6 2687 (2000).
142. G Wang, E Gunic, J-L Girardet, V Stoisavljevic Bioorg. Med. Chem. Lett. 9 1147 (1999).
143. K Morita, C Hasegawa, M Kaneko, S Tsutsumi, J Sone, T Ishikawa, T Imanishi, M Koizumi Nucleic Acids Suppl. 1 241 (2001).
144. K Morita, C Hasegawa, M Kaneko, S Tsutsumi, J Sone, T Ishikawa, T Imanishi, M Koizumi Bioorg. Med. Chem. Lett. 12 73 (2002).
145. K Morita, M Takagi, C Hasegawa, M Kaneko, S Tsutsumi, J Sone, T Ishikawa, T Imanishi, M Koizumi Bioorg. Med. Chem. 11 2211 (2003).
146. Y Hari, S Obika, R Ohnishi, K Eguchi, T Osali, H Ohishi, T Imanishi Bioorg. Med. Chem. 14 1029 (2006).
147. M Koizumi, K Morita, M Daigo, S Tsutsumi, K Abe, S Obika, T Imanishi Nucleic Acids Res. 31 3267 (2003).
148. M Koizumi Biol. Pharm. Bull. 27 453 (2004).
149. M Horie, K Morita, J Kawakami, O Ando, M Koizumi Nucleosides, Nucleotides Nucleic Acids 25 231 (2006).
150. K Morita, KYamate, S-I Kurakata, K Watanabe, T Imanishi, M Koizumi Nucleosides, Nucleotides Nucleic Acids 22 1619 (2003).
151. A Surono, T V Khanh, Y Takeshima, H Wada, M Yagi, M Takagi, M Koizumi, M Matsuo Human Gene Ther. 15 749 (2004).
152. K Morita, K Yamate, S-i Kurakata, K Abe, K Watanabe, M Koizumi, T Imanishi Nucleosides, Nucleotides Nucleic Acids 25 503 (2006).
153. M Koizumi, M Takagi-Sato, R Okuyama, K Araki, W Sun, D Nakai Nucleic Acids Symp. Ser. 51 111 (2007).
154. M Koizumi, K Morita, M Takagi, H Yasumo, A Kasuya Anal. Biochem. 340 287 (2005).
155. M Koizumi Curr. Opin. Mol. Ther. 8 144 (2006).
156. M Takagi-Sato, S Tokihiro, R Kawaida, M Koizumi Oligonucleotides 17 291 (2007).
157. E De Clercq J. Clin. Virol. 30 115 (2004).
158. C Mathé, C Périgaud Eur. J. Org. Chem. 1489 (2008).
159. P I Pradeepkumar, P Cheruku, O Plashkevych, P Acharya, S Gohil, J Chattopodhyaya J. Am. Chem. Soc. 126 11484 (2004).
160. D Honcharenko, O P Varghese, O Plashkevych, J Barman, J Chattopadhyaya J. Org. Chem. 71 299 (2006).
161. N Albæk, M Petersen, P Nielsen J. Org. Chem. 71 7731 (2006).
162. P Srivastava, J Barman, W Pathmasiri, O Plashkevych, M Wenska, J Chattopadhyaya J. Am. Chem. Soc. 129 8362 (2007).
163. C Zhou, Y Liu, M Andaloussi, N Badgujar, O Plashkevych, J Chattopadhyaya J. Org. Chem. 74 118 (2009).
164. H Kaur, B R Babu, S Maiti Chem. Rev. 107 4672 (2007).
165. P Herdewijn Antiviral Res. 71 317 (2006).
166. A Van Aerschot, A Marchand, G Schepers, W Van den Eynde, J Rozenski, R Busson, P Herdewijn Nucleosides, Nucleotides Nucleic Acids 22 1227 (2003).
167. K Nauwelaerts, E Lescrinier, G Sclep, P Herdewijn Nucleic Acids Res. 33 2452 (2005).
168. D D'Alonzo, A Guaragna, A Van Aerschot, P Herdewijn, G Palumbo Tetrahedron Lett. 49 6068 (2008).
169. P Gu, G Schepers, J Rozenski, A Van Aerschot, P Herdewijn Oligonucleotides 13 479 (2003).
170. K Robeyns, P Herdewijn, L Van Meervelt J. Am. Chem. Soc. 130 1979 (2008).
171. D D'Alonzo, A Van Aerschot, A Guaragna, G Palumbo, G Schepers, S Capone, J Rozenski, P Herdewijn Chem. - Eur. J. 15 10121 (2009).
172. P E Nielsen Acc. Chem. Res. 32 624 (1999).
173. V V Demidov, M D Frank-Kamenetskii Trends Biochem. Sci. 29 62 (2004).
174. V A Efimov, O G Chakhmakhcheva, E Wickstrom Nucleosides, Nucleotides Nucleic Acids 24 1853 (2005).
175. V A Kumar, K N Ganesh Acc. Chem. Res. 38 404 (2005).
176. J I Yeh, B Shivachev, S Rapireddy, M J Crawford, R R Gil, S Du, M Madrid, D H Ly J. Am. Chem. Soc. 132 10717 (2010).
177. V A Efimov, A A Buryakova, M V Chub, O G Chakhmakhcheva Bioorg. Khim. 24 696 (1998) a.
178. V A Efimov, M V Choob, A A Buryakova, O G Chakhmakhcheva Nucleosides Nucleotides 17 1671 (1998).
179. V A Efimov, A A Buryakova, M V Choob, O G Chakhmakhcheva Nucleosides Nucleotides 18 1393 (1999).
180. V A Efimov, V N Klykov, O G Chakhmakhcheva Nucleosides, Nucleotides Nucleic Acids 22 593 (2003).
181. V A Efimov, M V Choob, A A Buryakova, A L Kalinkina, O G Chakhmakhcheva Nucleic Acids Res. 26 566 (1998).
182. V A Efimov, A A Buryakova, M V Chub, O G Chakhmakhcheva Bioorg. Khim. 25 611 (1999) a.
183. V Efimov, M Choob, A Buryakova, D Phelan, O Chakhmakhcheva Nucleosides, Nucleotides Nucleic Acids20 419 (2001).
184. V A Efimov, A A Buryakova, O G Chakhmakhcheva Nucleic Acids Res. 27 4416 (1999).
185. V A Efimov, O G Chakhmakhcheva Bioorg. Khim. 25 848 (1999) a.
186. D Phelan, K Hondorp, M Choob, V Efimov, J Fernandez Nucleosides, Nucleotides Nucleic Acids 20 1107 (2001).
187. V A Efimov, K R Birikh, D B Staroverov, S A Lukyanov, M B Tereshina, A G Zaraisky, O G Chakhmakhcheva Nucleic Acids Res. 34 2247 (2006).
188. V A Efimov, V N Klykov, O G Chakhmakhcheva Nucleosides, Nucleotides Nucleic Acids 26 1595 (2007).
189. D Rejman, P Kočalka, M Buděšínský, R Pohl, I Rosenberg Tetrahedron 63 1243 (2007).
190. D Rejman, P Kočalka, R Pohl, Z Točik, I Rosenberg Collect. Czech. Chem. Commun. 74 935 (2009).
191. V Vaněk, M Buděšínský, M Rinnová, I Rosenberg Tetrahedron 65 862 (2009).
192. D Rejman, R Pohl, P Kočalka, M Masojídková, I Rosenberg Tetrahedron 65 3673 (2009).
193. V A Efimov, A V Aralov, O G Chakhmakhcheva Bioorg. Khim. 36 725 (2010) a.
194. P E Nielsen, M Egholm, O Buchardt Bioconjugate Chem. 5 3 (1994).
195. V A Kumar Nucleosides, Nucleotides Nucleic Acids 22 1045 (2003).
196. R Corradini, S Sforza, T Tedeschi, F Totsingan, R Marchelli Curr. Top. Med. Chem. 7 681 (2007).
197. V A Kumar Eur. J. Org. Chem. 2021 (2002).
198. B P Gangamani, V A Kumar, K N Ganesh Tetrahedron 55 177 (1999).
199. Meena, V A Kumar, K N Ganesh Nucleosides, Nucleotides Nucleic Acids 20 1193 (2001).
200. Meena, V A Kumar Bioorg. Med. Chem. 11 3393 (2003).
201. M D'Costa, V A Kumar, K N Ganesh Org. Lett. 1 1513 (1999).
202. M D'Costa, V A Kumar, K N Ganesh Org. Lett. 3 1281 (2001).
203. V A Kumar, M D'Costa, K N Ganesh Nucleosides, Nucleotides Nucleic Acids 20 1187 (2001).
204. Y Li, T Jin, K Liu Nucleosides, Nucleotides Nucleic Acids 20 1705 (2001).
205. T Vilaivan, C Khongdeesameor, P Harnyuttanakorn, M S Westwell, G Lowe Bioorg. Med. Chem. Lett. 10 2541 (2000).
206. T Vilaivan, C Suparpprom, P Harnyuttanakorn, G Lowe Tetrahedron Lett. 42 5533 (2001).
207. T Vilaivan, G Lowe J. Am. Chem. Soc. 124 9326 (2002).
208. C Suparpprom, C Srisuwannaket, P Sangvanich, T Vilaivan Tetrahedron Lett. 46 2833 (2005).
209. T Vilaivan, C Srisuwannaket Org. Lett. 8 1897 (2006).
210. N K Sharma, K N Ganesh Chem. Commun. 2484 (2003).
211. N K Sharma, K N Ganesh Tetrahedron Lett. 45 1403 (2004).
212. A Püschl, T Boesen, G Zuccarello, O Dahl, S Pitsch, P E Nielsen J. Org. Chem. 66 707 (2001).
213. A Püschl, T Tedeschi, P E Nielsen Org. Lett. 2 4161 (2000).
214. V Kumar, P S Pallan, Meena, K N Ganesh Org. Lett. 3 1269 (2001).
215. D T Hickman, P M King, M A Cooper, J M Slaterb, J Micklefield Chem. Commun. 2251 (2000).
216. D T Hickman, T H S Tan, J Morral, P M King, M A Cooper, J Micklefield Org. Bioorg. Chem. 1 3277 (2003).
217. T H S Tan, D T Hickman, J Morral, I G Beadham, J Micklefield Chem. Commun. 516 (2004).
218. T H S Tan, R J Worthington, R G Pritchard, J Morral, J Micklefield Org. Biomol. Chem. 5 239 (2007).
219. R J Worthington, A P O'Rourke, J Morral, T H S Tan, J Micklefield Org. Biomol. Chem. 5 249 (2007).
220. A I Khan, T H S Tan, J Micklefield Chem. Commun. 1436 (2006).
221. R J Worthington, N M Bell, R Wong, J Micklefield Org. Biomol. Chem. 6 92 (2008).
222. V A Kumar, Meena Nucleosides, Nucleotides Nucleic Acids 22 1101 (2003).
223. T Govidaraju, V A Kumar Chem. Commun. 495 (2005).
224. P S Lonkar, K N Ganesh, V A Kumar Org. Biomol. Chem. 2 2604 (2004).
225. P S Lonkar, V A Kumar, K N Ganesh Nucleosides, Nucleotides Nucleic Acids 20 1197 (2001).
226. P S Lonkar, V A Kumar J. Org. Chem. 70 6956 (2005).
227. P S Shirude, V A Kumar, K N Ganesh Tetrahedron Lett. 45 3085 (2004).
228. P S Shirude, V A Kumar, K N Ganesh Tetrahedron 60 9485 (2004).
229. P S Lonkar, V A Kumar Nucleosides, Nucleotides Nucleic Acids 22 1105 (2003).
230. P S Lonkar, V A Kumar Bioorg. Med. Chem. Lett. 14 2147 (2004).
231. E Lescrinier, M Froeyen, P Herdewijn Nucleic Acids Res. 31 2975 (2003).
232. T Govindaraju, RG Gonnade, MM Bhadbhade, VA Kumar, K N Ganesh Org. Lett. 5 3013 (2003).
233. T Govindaraju, V A Kumar, K N Ganesh Chem. Commun. 860 (2004).
234. T Govindaraju, V A Kumar, K N Ganesh J. Org. Chem. 69 1858 (2004).
235. T Govindaraju, V A Kumar, K N Ganesh J. Am. Chem. Soc. 127 4144 (2005).
236. T Govindaraju, V A Kumar, K N Ganesh J. Org. Chem. 69 5725 (2004).
237. T Govindaraju, V Madhuri, V A Kumar, K N Ganesh J. Org. Chem. 71 14 (2006).
238. M C Myers, M A Witschi, N V Larionova, J M Franck, R D Haynes, T Hara, A Grajkowski, D H Appella Org. Lett. 5 2695 (2003).
239. J K Pokorski, M A Witschi, B L Purnell, D H Appella J. Am. Chem. Soc. 126 15067 (2004).
240. J K Pokorski, M C Myers, D H Appella Tetrahedron Lett. 46 915 (2005).
241. E A Englund, Q Xu, M A Witschi, D H Appella J. Am. Chem. Soc. 128 16456 (2006).
242. JK Pokorski, J-M Nam, RAVega, CA Mirkin, D H Appella Chem. Commun. 2101 (2005).
243. N Zhang, D H Appella J. Am. Chem. Soc. 129 8424 (2007).
244. L Kovács, M Hornyák, N M Howarth Nucleosides, Nucleotides Nucleic Acid 22 1363 (2003).
245. N M Howarth, L P G Wakelin, D M Walker Nucleosides, Nucleotides Nucleic Acids 22 1352 (2003).
246. P Herdewijn, P Marliére Chem. Biodiv. 6 791 (2009).
247. D H Appella Curr. Opin. Chem. Biol. 13 687 (2009).
248. S Sforza, G Haaima, R Marchelli, P E Nielsen Eur. J. Org. Chem. 197 (1999).
249. V Menchise, G De Simone, T Tedeschi, R Corradini, S Sforza, R Marchelli, D Capasso, M Saviano, C Pedone Proc. Natl. Acad. Sci. USA 100 12021 (2003).
250. T Tedeski, S Sforza, A Dossena, R Corradini, R Marchelli Chirality 17 S196 (2005).
251. S Sforza, R Corradini, S Ghirardi, A Dossena, R Marchelli Eur. J. Org. Chem. 2905 (2000).
252. R Corradini, G Feriotto, S Sforza, R Marchelli, R Gambari J. Mol. Recognit. 17 76 (2004).
253. T Tedeschi, M Chiari, G Galaverna, S Sforza, M Cretich, R Corradini, R Marchelli Electrophoresis 26 4310 (2005).
254. S Sforza, T Tedeschi, R Corradini, D Ciavardelli, A Dossena, R Marchelli Eur. J. Org. Chem. 1056 (2003).
255. T Tedeschi, S Sforza, R Corradini, R Marchelli Tetrahedron Lett. 46 8395 (2005).
256. S Sforza, T Tedeschi, R Corradini, R Marchelli Nucleic Acids Symp. Ser. 51 19 (2007).
257. T Ishizuka, J Yoshida, YYamamoto, J Sumaoka, T Tedeschi, R Corradini, S Sforza, M Komiyama Nucleic Acids Res. 36 1464 (2008).
258. T Ishizuka, T Tedeschi, R Corradini, M Komiyama, S Sforza, R Marchelli ChemBioChem 10 2607 (2009).
259. P Zhou, M Wang, L Du, G W Fisher, A Waggoner, D H Ly J. Am. Chem. Soc. 125 6878 (2003).
260. A Dragulescu-Andrasi, P Zhou, G He, D H Ly Chem. Commun. 244 (2005).
261. P Zhou, A Dragulescu-Andrasi, B Bhattacharya, H O'Keefe, P Vatta, J J Hyldig-Nielsen, D H Ly Bioorg. Med. Chem. Lett. 16 4931 (2006).
262. A Dragulescu-Andrasi, S Rapireddy, G He, B Bhattacharya, J J Hyldig-Nielsen, G Zon, D H Ly J. Am. Chem. Soc. 128 16104 (2006).
263. ADragulescu-Andrasi, S Rapireddy, BM Frezza, C Gayathri, R R Gil, D H Ly J. Am. Chem. Soc. 128 10258 (2006).
264. S Rapireddy, G He, S Roy, B A Armitage, D H Ly J. Am. Chem. Soc. 129 15596 (2007).
265. V Chenna, S Rapireddy, B Sahu, C Ausin, E Pedroso, D H Ly ChemBioChem 9 2388 (2009).
266. G He, S Rapireddy, R Bahal, B Sahu, D H Ly J. Am. Chem. Soc. 131 12088 (2009).
267. B Sahu, V Chenna, K L Lathrop, S M Thomas, G Zon, K J Livak, D H Ly J. Org. Chem. 74 1509 (2009).
268. E A Englund, D H Appella Org. Lett. 7 3465 (2005).
269. C Dose, O Seitz Org. Lett. 7 4365 (2005).
270. US P. 5034506 (1991).
271. US P. 5185444 (1993).
272. J E Summerton Lett. Pept. Sci. 10 215 (2003).
273. J E Summerton. Curr. Top. Med. Chem. 7 651 (2007).
274. B R Bill, A M Petzold, K J Clark, L A Schimmenti, S C Ekker Zebrafish 6 69 (2009).
275. O Chakhmakhcheva, M Andrianov, A Buryakova, M Choob, V Efimov Nucleosides Nucleotides 18 1427 (1999).
276. T V Abramova, M F Kassakin, A A Lomzov, D V Pyshnyi, V N Silnikov Bioorg. Chem. 35 258 (2007).
277. T V Abramova, M F Kassakin, V N Silnikov Indian J. Chem., Sect. B 48 1721 (2009).
278. N Zhang, C Tan, P Cai, Y Jiang, P Zhang, Y Zhao Tetrahedron Lett. 49 3570 (2008).
279. N Zhang, C Tan, P Cai, P Zhang, Y Zhao, Y Jiang Bioorg. Med. Chem. 17 2441 (2009).
280. S Pérez-Rentero, J Alguacil, J Robles Tetrahedron 65 1171 (2009).
281. D L Swenson, K L Warfild, T K Warren, C Lovejoy, J N Hassinger, G Ruthel, R E Blouch, H M Moulton, D D Weller, P L Iversen, S Bavari Antimicrob. Agents Chemother. 53 2089 (2009).
282. B L Mellbye, D D Weller, J N Hassinger, M D Reeves, C E Lovejoy, P L Iversen, B L Geller J. Antimicrob. Chemother. 65 98 (2010).
283. J D Moulton, S Jiang Molecules 14 1304 (2009).
284. P Sazani, S-H Kang, M A Maier, C Wei, J Dillman, J Summerton, M Manoharan, R Kole Nucleic Acids Res. 29 3965 (2001).
285. J B Bramsen, M B Laursen, A F Nielsen, T B Hansen, C Bus, N Langkjær, B R Babu, T Højland, M Abramov, A Van Aerschot, D Odadzic, R Smicius, J Haas, C Andree, J Barman, M Wenska, P Srivastava, C Zhou, D Honcharenko, S Hess, EMüller, G V Bobkov, S N Mikhailov, E Fava, T F Meyer, J Chattopadhyaya, M Zerial, J W Engels, P Herdewijn, J Wengel, J Kjems Nucleic Acids Res. 37 2867 (2009).