1932
0
  1. Home
  2. A-Z Publications
  3. Annual Review of Biochemistry
  4. Volume 67, 1998
  5. Article

Annual Review of Biochemistry

Volume 67, 1998

MODIFIED OLIGONUCLEOTIDES: Synthesis and Strategy for Users

Abstract

Synthetic oligonucleotide analogs have greatly aided our understanding of several biochemical processes. Efficient solid-phase and enzyme-assisted synthetic methods and the availability of modified base analogs have added to the utility of such oligonucleotides. In this review, we discuss the applications of synthetic oligonucleotides that contain backbone, base, and sugar modifications to investigate the mechanism and stereochemical aspects of biochemical reactions. We also discuss interference mapping of nucleic acid–protein interactions; spectroscopic analysis of biochemical reactions and nucleic acid structures; and nucleic acid cross-linking studies.

The automation of oligonucleotide synthesis, the development of versatile phosphoramidite reagents, and efficient scale-up have expanded the application of modified oligonucleotides to diverse areas of fundamental and applied biological research. Numerous reports have covered oligonucleotides for which modifications have been made of the phosphodiester backbone, of the purine and pyrimidine heterocyclic bases, and of the sugar moiety; these modifications serve as structural and mechanistic probes. In this chapter, we review the range, scope, and practical utility of such chemically modified oligonucleotides. Because of space limitations, we discuss only those oligonucleotides that contain phosphate and phosphate analogs as internucleotidic linkages.

Keyword(s): backbone modifications, base modifications, oligonucleotide analogs, reporter groups, sugar modifications
Loading

Article metrics loading...

/content/journals/10.1146/annurev.biochem.67.1.99
1998-07-01
2024-04-24
Loading full text...

Full text loading...

/deliver/fulltext/biochem/67/1/annurev.biochem.67.1.99.html?itemId=/content/journals/10.1146/annurev.biochem.67.1.99&mimeType=html&fmt=ahah

Literature Cited

  1. Caruthers MH, Beaton G, Wu JV, Wiesler W. 1992. Methods Enzymol. 211:3–20
  2. Beaucage SL. 1993. Methods Mol. Biol. 20:33–61
  3. Brown T, Brown DJS. 1991. In Oligonucleotides and Analogues. A Practical Approach, ed. F Eckstein 1–24 Oxford: IRL
  4. Wincott F, Direnzo A, Grimm S, Tracz D, Workman C. et al. 1995. Nucleic Acids Res. 23:2677–84
  5. Davis RH. 1995. Curr. Opin. Biotechnol. 6:213–17
  6. Gait MJ, Pritchard C, Slim G. 1991. See Ref. 3 25–48
  7. Zon G, Stec WJ. 1991. See Ref. 3 87–108
  8. Wiesler WT, Marshall WS, Caruthers MH. 1993. Methods Mol. Biol. 20:191–206
  9. Miller PS, Cushman CD, Levis JT. 1991. See Ref. 3 137–54
  10. Maunders MJ. 1993. Methods Mol. Biol. 16:213–30
  11. Yu YT, Steitz JA. 1997. RNA 3:807–10
  12. Eggerding FA, Iovannisci DM, Brinson E, Grossman P, Winn-Deen ES. 1995. Hum. Mutat. 5:153–65
  13. Martinelli RA, Arruda JC, Dwivedi P. 1996. Clin. Chem. 42:14–18
  14. Barrio JR, Barrio MCG, Leonard NJ, England TE, Uhlenbeck OC. 1978. Biochemistry 17:2077–81
  15. Voegel JJ, Benner SA. 1996. Helv. Chim. Acta 79:1881–98
  16. Cosstick R, McLaughlin LW, Eckstein F. 1984. Nucleic Acids Res. 12:1791–810
  17. Kinoshita Y, Nishigaki K, Husimi Y. 1996. Chem. Lett. 9:797–98
  18. Breitschopf K, Gross HJ. 1996. Nucleic Acids Res. 24:405–10
  19. Ohtsuki T, Kawai G, Watanabe Y, Kita K, Nishikawa K, Watanabe K. 1996. Nucleic Acids Res. 24:662–67
  20. Moore MJ, Sharp PA. 1992. Science 256:992–97
  21. Bain JD, Switzer C. 1992. Nucleic Acids Res. 20:4372
  22. Eckstein F. 1985. Annu. Rev. Biochem. 54:367–402
  23. Griffiths AD, Potter BVL, Eperon IC. 1987. Nucleic Acids Res. 15:4145–62
  24. Hacia JG, Wold BJ, Dervan PB. 1994. Biochemistry 33:5367–69
  25. Tang JY, Roskey A, Li Y, Agrawal S. 1995. Nucleosides Nucleotides 14:985–90
  26. Milligan JF, Uhlenbeck OC. 1989. Methods Enzymol. 180:51–62
  27. Conrad E, Hanne A, Gaur RK, Krupp G. 1995. Nucleic Acids Res. 23:1845–53
  28. Sousa R, Padilla R. 1995. EMBO J. 14:4609–21
  29. Aurup H, Williams DM, Eckstein F. 1992. Biochemistry 31:9636–41
  30. Huang Y, Eckstein F, Padilla R, Sousa R. 1997. Biochemistry 36:8231–42
  31. Burgin AB, Pace NR. 1990. EMBO J. 9:4111–18
  32. Zhang-Keck Z-y, Eckstein F, Washington LD, Stallcup MR. 1988. J. Biol. Chem. 263:9550–56
  33. Igloi G. 1988. Biochemistry 27:3842–49
  34. Logsdon N, Lee CGL, Harper JW. 1992. Anal. Biochem. 205:36–41
  35. Vaish NK, Heaton PA, Eckstein F. 1997. Biochemistry 36:6495–501
  36. Goodchild J. 1990. Bioconjug. Chem. 1:165–87
  37. Bongartz JP, Aubertin AM, Milhaud PG, Lebleu B. 1994. Nucleic Acids Res. 22:4681–88
  38. Soukchareun S, Tregear GW, Haralambidis J. 1995. Bioconjug. Chem. 6:43–53
  39. Corey DR, Munoz-Medellin D, Huang A. 1995. Bioconjug. Chem. 6:93–100
  40. Ruth JL. 1994. Methods Mol. Biol. 26:167–85
  41. Hangeland JJ, Levis JT, Lee YC, T′so POP. 1995. Bioconjug. Chem. 6:695–701
  42. Shea RG, Marsters JC, Bischofberger N. 1990. Nucleic Acids Res. 18:3777–83
  43. Buijsman RC, Kuijpers WHA, Basten JEM, Kuylyeheskiely E, Vandermarel GA. et al. 1996. Chemistry 2:1572–77
  44. Will DW, Brown T. 1992. Tetrahedron Lett. 33:2729–32
  45. Letsinger RL, Zhang G, Sun DK, Ikeuchi T, Sarin PS. 1989. Proc. Natl. Acad. Sci. USA 86:6553–56
  46. Zelphatti O, Wagner E, Leserman L. 1994. Antiviral Res. 25:13–25
  47. Henderson GB, Stein CA. 1995. Nucleic Acids Res. 23:3726–31
  48. Hagmar P, Bailey M, Tong G, Haralambidis J, Sawyer WH, Davidson BE. 1995. Biochim. Biophys. Acta Gen. Subj. 1244:259–68
  49. Soukup GA, Cerny RL, Maher LJ. 1995. Bioconjug. Chem. 6:135–38
  50. Holtke HJ, Ankenbauer W, Muhlegger K, Rein R, Sagner G. et al. 1995. Cell. Mol. Biol. 41:883–905
  51. Stec WJ, Grajkowski A, Kobylanska A, Karwowski B, Koziolkiewicz M. et al. 1995. J. Am. Chem. Soc. 117:12019–29
  52. Connolly BA, Potter BVL, Eckstein F, Pingoud A, Grotjahn L. 1984. Biochemistry 23:3443–53
  53. Grasby JA, Connolly BA. 1992. Biochemistry 31:7855–61
  54. Engelman A, Mizuuchi K, Craigie R. 1991. Cell 67:1211–21
  55. Mizuuchi K, Adzuma K. 1991. Cell 66:129–40
  56. Kurpiewski MR, Koziolkiewicz M, Wilk A, Stec WJ, Jen-Jacobson L. 1996. Biochemistry 35:8846–54
  57. Thorogood H, Grasby JA, Connolly BA. 1996. J. Biol. Chem. 271:8855–62
  58. McSwiggen JA, Cech TR. 1989. Science 244:679–83
  59. Rajagopal J, Doudna JA, Szostak JW. 1989. Science 244:692–94
  60. Moore MJ, Sharp PA. 1993. Nature 365:364–68
  61. Maschhoff KL, Padgett RA. 1993. Nucleic Acids Res. 21:5456–62
  62. Chanfreau G, Jacquier A. 1994. Science 266:1383–87
  63. Padgett RA, Podar M, Boulanger SC, Perlman PS. 1994. Science 266:1685–88
  64. Sharp PA. 1994. Cell 77:805–15
  65. van Tol H, Buzayan JM, Feldstein PA, Eckstein F, Bruenig G. 1990. Nucleic Acids Res. 18:1971–75
  66. Slim G, Gait MJ. 1991. Nucleic Acids Res. 19:1183–88
  67. Pley HW, Flaherty KM, McKay DB. 1994. Nature 372:68–74
  68. Scott WG, Finch JT, Klug A. 1995. Cell 81:991–1002
  69. Kitts PA, Nash HA. 1988. J. Mol. Biol. 204:95–107
  70. Herschlag D, Piccirilli JA, Cech TR. 1991. Biochemistry 30:4844–54
  71. Polesky AH, Dahlberg ME, Benkovic SJ, Grindley NDF, Joyce CM. 1992. J. Biol. Chem. 267:8417–28
  72. Noel JP, Hamm HE, Sigler PB. 1993. Nature 366:654–63
  73. Gish G, Eckstein F. 1988. Science 240:1520–22
  74. Schatz D, Leberman R, Eckstein F. 1991. Proc. Natl. Acad. Sci. USA 88:6132–36
  75. Waring RB. 1989. Nucleic Acids Res. 17:10281–93
  76. Christian EL, Yarus M. 1993. Biochemistry 32:4475–80
  77. Jaffe EK, Cohn M. 1979. J. Biol. Chem. 254:10839–45
  78. Pecoraro VL, Hermes JD, Cleland WW. 1984. Biochemistry 23:5262–71
  79. Milligan JF, Uhlenbeck OC. 1989. Biochemistry 28:2849–55
  80. Biou V, Yaremchuk A, Tukalo M, Cusack S. 1994. Science 263:1404–10
  81. Rudinger J, Puglisi JD, Pütz J, Schatz D, Eckstein F. et al. 1992. Proc. Natl. Acad. Sci. USA 89:5882–86
  82. Kreutzer R, Kern D, Giege R, Rudinger J. 1995. Nucleic Acids Res. 23:4598–4602
  83. Caprara MG, Mohr G, Lambowitz AM. 1996. J. Mol. Biol. 257:512–31
  84. Caprara MG, Lehnert V, Lambowitz AM, Westhof E. 1996. Cell 87:1135–45
  85. Dabrowski M, Spahn CMT, Nierhaus KH. 1995. EMBO J. 14:4872–82
  86. Harris ME, Pace NR. 1995. RNA 1:210–18
  87. Hardt WD, Warnecke JM, Erdmann VA, Hartmann RK. 1995. EMBO J. 14:2935–44
  88. Warnecke JM, Fürste JP, Hardt WD, Erdmann VA, Hartmann RK. 1996. Proc. Natl. Acad. Sci. USA 93:8924–28
  89. Chen Y, Li XQ, Gegenheimer P. 1997. Biochemistry 36:2425–38
  90. Strobel SA, Shetty K. 1997. Proc. Natl. Acad. Sci. USA 94:2903–8
  91. Ruffner DE, Uhlenbeck OC. 1990. Nucleic Acids Res. 18:6025–29
  92. Knöll R, Bald R, Fürste JP. 1997. RNA 3:132–40
  93. Scott WG, Murray JB, Arnold JRP, Stoddard BL, Klug A. 1996. Science 274:2065–69
  94. Dahm SC, Uhlenbeck OC. 1991. Biochemistry 30:9464–69
  95. Mitrasinovic O, Epstein LM. 1997. Nucleic Acids Res. 25:2189–96
  96. Jeoung Y-H, Kumar PKR, Suh Y-A, Taira K, Nishikawa S. 1994. Nucleic Acids Res. 22:3722–27
  97. De Clercq E, Eckstein F, Sternbach H, Merigan TC. 1970. Virology 42:421–28
  98. Agrawal S. 1996. Trends Biotechnol. 14:376–87
  99. Huang JC, Svoboda DL, Reardon JT, Sancar A. 1992. Proc. Natl. Acad. Sci. USA 89:3664–68
  100. Reardon JT, Thompson LH, Sancar A. 1997. Nucleic Acids Res. 25:1015–21
  101. Gupta AP, Benkovic PA, Benkovic SJ. 1984. Nucleic Acids Res. 12:5897–911
  102. Skerra A. 1992. Nucleic Acids Res. 20:3551–54
  103. Nakamaye K, Eckstein F. 1986. Nucleic Acids Res. 14:9679–98
  104. Sayers JR, Schmidt W, Eckstein F. 1988. Nucleic Acids Res. 16:791–801
  105. Olsen DB, Kotzorek G, Eckstein F. 1990. Biochemistry 29:9546–51
  106. Walker GT, Nadeau JG, Spears PA, Schram JL, Nycz CM, Shank DD. 1994. Nucleic Acids Res. 22:2670–77
  107. Walter NG, Strunk G. 1994. Proc. Natl. Acad. Sci. USA 91:7937–41
  108. Musier-Forsyth K, Schimmel P. 1994. Biochemistry 33:773–79
  109. Fidanza JA, Ozaki H, McLaughlin LW. 1992. J. Am. Chem. Soc. 114:5509–17
  110. Yang W, Steitz TA. 1995. Cell 82:193–207
  111. König P, Giraldo R, Chapman L, Rhodes D. 1996. Cell 85:125–36
  112. Francois J-C, Saison-Behmoaras T, Barbier C, Chassignol M, Thuong NT, Helene C. 1989. Proc. Natl. Acad. Sci. USA 86:9702–6
  113. Gryaznov SM, Letsinger RL. 1993. Nucleic Acids Res. 21:1403–8
  114. Chu BCF, Orgel LE. 1990. DNA Cell Biol. 9:71–76
  115. Kang S-H, Xu X, Heidenreich O, Gryaznov S, Nerenberg M. 1995. Nucleic Acids Res. 23:2344–45
  116. Gryaznov SM, Letsinger RL. 1993. J. Am. Chem. Soc. 115:3808–9
  117. Mag M, Schmidt R, Engels JW. 1992. Tetrahedron Lett. 33:7319–22
  118. Bannwarth W. 1988. Helv. Chim. Acta 71:1517–27
  119. Mag M, Engels JW. 1989. Nucleic Acids Res. 17:5973–88
  120. Letsinger RL, Mungall WS. 1970. J. Org. Chem. 35:3800–3
  121. Chen J-K, Schultz RG, Lloyd DH, Gryaznov SM. 1995. Nucleic Acids Res. 23:2661–68
  122. Gryaznov S, Skorski T, Cucco C, Nieborowska-Skorska M, Chiu CY. et al. 1996. Nucleic Acids Res. 24:1508–14
  123. Mag M, Lüking S, Engels JW. 1991. Nucleic Acids Res. 19:1437–41
  124. Vyle JS, Connolly BA, Kemp D, Cosstick R. 1992. Biochemistry 31:3012–18
  125. Szczelkun MD, Connolly BA. 1995. Biochemistry 34:10724–33
  126. Burgin AB, Huizenga BN, Nash HA. 1995. Nucleic Acids Res. 23:2973–79
  127. Dantzman CL, Kiessling LL. 1996. J. Am. Chem. Soc. 118:11715–19
  128. Piccirilli JA, Vyle JS, Caruthers MH, Cech TR. 1993. Nature 361:85–88
  129. Weinstein LB, Jones BCNM, Cosstick R, Cech TR. 1997. Nature 388:805–8
  130. Kuimelis RG, McLaughlin LW. 1996. J. Am. Chem. Soc. 35:5308–17
  131. Zhou D-M, Usman N, Wincott FE, Matulic-Adamic J, Orita M. et al. 1996. J. Am. Chem. Soc. 118:5862–66
  132. Thomson JB, Patel BK, Jimenez V, Eckart K, Eckstein F. 1996. J. Org. Chem. 61:6273–81
  133. Beaton G, Dellinger D, Marshall WS, Caruthers MH. 1991. See Ref. 3 109–35
  134. Wiesler WT, Caruthers MH. 1996. J. Org. Chem. 61:4272–81
  135. Greef CH, Seeberger PH, Caruthers MH, Beaton G, Bankaitisdavis D. 1996. Tetrahedron Lett. 37:4451–54
  136. Cummins L, Graff D, Beaton G, Marshall WS, Caruthers MH. 1996. Biochemistry 35:8734–41
  137. Piotto ME, Granger JN, Cho Y, Gorenstein DG. 1990. J. Am. Chem. Soc. 112:8632–34
  138. Tonkinson JL, Guvakova M, Khaled Z, Lee J, Yakubov L. et al. 1994. Antisense Res. Dev. 4:269–74
  139. Vaughn JP, Stekler J, Demirdji S, Mills JK, Caruthers MH. et al. 1996. Nucleic Acids Res. 24:4558–64
  140. Marshall WS, Caruthers MH. 1993. Science 259:1564–70
  141. Krieg AM, Matson S, Fisher E. 1996. Antisense Nucleic Acid Drug Dev. 6:133–39
  142. Pirrung MC, Chidambaram N. 1996. J. Org. Chem. 61:1540–42
  143. Reynolds MA, Hogrefe RI, Jaeger JA, Schwartz DA, Riley TA. et al. 1996. Nucleic Acids Res. 24:4584–91
  144. Mujeeb A, Reynolds MA, James TL. 1997. Biochemistry 36:2371–79
  145. Kean JM, Kipp SA, Miller PS, Kulka M, Aurelian L. 1995. Biochemistry 34:14617–20
  146. Delong RK, Miller PS. 1996. Antisense Nucleic Acid Drug Dev. 6:273–80
  147. Reynolds MA, Arnold LJ, Almazan MT, Beck TA, Hogrefe RI. et al. 1994. Proc. Natl. Acad. Sci. USA 91:12433–37
  148. Strauss JK, Maher LJ. 1994. Science 266:1829–34
  149. Strauss JK, Prakash TP, Roberts C, Switzer C, Maher LJ. 1996. Chem. Biol. 3:671–78
  150. Botfield MC, Weiss MA. 1994. Biochemistry 33:2349–55
  151. Hausheer FH, Singh UC, Palmer TC, Saxe JD. 1990. J. Am. Chem. Soc. 112:9468–74
  152. Duckett DR, Murchie AIH, Lilley DMJ. 1990. EMBO J. 9:583–90
  153. Seela F, Tran-Thi QH, Franzen D. 1982. Biochemistry 21:4338–43
  154. Seela F, Driller H. 1986. Nucleic Acids Res. 14:2319–32
  155. Seela F, Kehne A. 1985. Biochemistry 24:7556–61
  156. Seela F, Grein T. 1992. Nucleic Acids Res. 20:2297–2306
  157. Smith SA, Rajur SB, McLaughlin LW. 1994. Nat. Struct. Biol. 1:18–22
  158. Zhang XL, Gottlieb PA. 1993. Biochemistry 32:11374–84
  159. Duggan LJ, Hill TM, Wu S, Garrison K, Zhang XL, Gottlieb PA. 1995. J. Biol. Chem. 270:28049–54
  160. Lesser DR, Kurpiewski MR, Jen-Jacobson L. 1990. Science 250:776–86
  161. Aiken CR, Gumport RI. 1991. Methods Enzymol. 208:433–57
  162. Murchie AIH, Lilley DMJ. 1994. EMBO J. 13:993–1001
  163. Kim MG, Zhurkin VB, Jernigan RL, Camerini-Otero RD. 1995. J. Mol. Biol. 247:874–89
  164. Wieczorek A, Dinter-Gottlieb G, Gottlieb PA. 1994. Bioorg. Med. Chem. Lett. 4:987–94
  165. Murchie AIH, Lilley DMJ. 1992. Nucleic Acids Res. 20:49–53
  166. Bevers S, Xiang GB, McLaughlin LW. 1996. Biochemistry 35:6483–90
  167. Newman PC, Nwosu VU, Williams DM, Cosstick R, Seela F, Connolly BA. 1990. Biochemistry 29:9891–901
  168. Limauro S, Benseler F, McLaughlin LW. 1994. Bioorg. Med. Chem. Lett. 4:2189–92
  169. Pütz J, Florentz C, Benseler F, Giege R. 1994. Struct. Biol. 1:580–82
  170. Adams CJ, Murray JB, Farrow FA, Arnold JRP, Stockley PG. 1995. Tetrahedron Lett. 36:5421–24
  171. Min CH, Cushing TD, Verdine GL. 1996. J. Am. Chem. Soc. 118:6116–20
  172. Cal S, Connolly BA. 1997. J. Biol. Chem. 272:490–96
  173. Tuschl T, Ng MMP, Pieken W, Benseler F, Eckstein F. 1993. Biochemistry 32:11658–68
  174. Grasby JA, Mersmann K, Singh M, Gait M. 1995. Biochemistry 34:4068–76
  175. Liu Q, Green JB, Khodadadi A, Haeberli P, Beigelman L, Pyle AM. 1997. J. Mol. Biol. 267:163–71
  176. Schweitzer BA, Kool ET. 1994. J. Org. Chem. 59:7238–42
  177. McKay DB. 1996. RNA 2:395–403
  178. McLaughlin LW, Wilson M, Ha SB. 1998. Comp. Nat. Prod. Chem. 7: In press
  179. Murray JB, Adams CJ, Arnold JRP, Stockley PG. 1995. Biochem. J. 311:487–94
  180. Burgin AB, Gonzalez C, Matulic-Adamic J, Karpeisky AM, Usman N. et al. 1996. Biochemistry 35:14090–97
  181. Mendelman LV, Kuimelis RG, McLaughlin LW, Richardson CC. 1995. Biochemistry 34:10187–93
  182. Wagner RW, Matteucci MD, Lewis JG, Gutierrez AJ, Moulds C, Froehler BC. 1993. Science 260:1510–13
  183. Moulds C, Lewis JG, Froehler BC, Grant D, Huang T. et al. 1995. Biochemistry 34:5044–53
  184. Flanagan WM, Kothavale A, Wagner RW. 1996. Nucleic Acids Res. 24:2936–41
  185. Wagner RW, Matteucci MD, Grant D, Huang T, Froehler BC. 1996. Nat. Biotechnol. 14:840–44
  186. Sala M, Pezo V, Pochet S, Wain-Hobson S. 1996. Nucleic Acids Res. 24:3302–6
  187. Loakes D, Brown DM. 1994. Nucleic Acids Res. 22:4039–43
  188. Loakes D, Brown DM, Linde S, Hill F. 1995. Nucleic Acids Res. 23:2361–66
  189. Nichols R, Andrews PC, Zhang P, Bergstrom DE. 1994. Nature 369:492–93
  190. Bergstrom DE, Zhang P, Toma PH, Andrews PC, Nichols R. 1995. J. Am. Chem. Soc. 117:1201–9
  191. Guo Z, Liu QH, Smith LM. 1997. Nat. Biotechnol. 15:331–35
  192. Perrachi A, Beigelman L, Usman N, Herschlag D. 1996. Proc. Natl. Acad. Sci. USA 93:11522–27
  193. Schmidt S, Beigelman L, Karpeisky A, Usman N, Sorensen US, Gait MJ. 1996. Nucleic Acids Res. 24:573–81
  194. Beigelman L, Karpeisky A, Usman N. 1994. Bioorg. Med. Chem. Lett. 4:1715–20
  195. Beigelman L, Karpeisky A, Matulic-Adamic J, Gonzalez C, Usman N. 1995. Nucleosides Nucleotides 14:907–10
  196. Saenger W. 1983. Principles of Nucleic Acid Structure. New York: Springer-Verlag [Google Scholar]
  197. Bratty J, Chartrand P, Ferbeyre G, Cedergren R. 1993. Biochim. Biophys. Acta 1216:345–59
  198. Yang J-H, Usman N, Chartrand P, Cedergren R. 1992. Biochemistry 31:5005–9
  199. Olsen DB, Benseler F, Aurup H, Pieken WA, Eckstein F. 1991. Biochemistry 30:9735–41
  200. Pieken WA, Olsen DB, Benseler F, Aurup H, Eckstein F. 1991. Science 253:314–17
  201. Paolella G, Sproat BS, Lamond AI. 1992. EMBO J. 11:1913–19
  202. Jarvis TC, Wincott FE, Alby LJ, McSwiggen JA, Beigelman L. et al. 1996. J. Biol. Chem. 29107–12
  203. Chowrira BM, Berzal-Herranz A, Keller CF, Burke JM. 1993. J. Biol. Chem. 268:19458–62
  204. Pyle AM, Cech TR. 1991. Nature 350:628–31
  205. Pyle AM, Murphy FL, Cech TR. 1992. Nature 358:123–28
  206. Herschlag D, Eckstein F, Cech TR. 1993. Biochemistry 32:8299–311
  207. Herschlag D, Eckstein F, Cech TR. 1993. Biochemistry 32:8312–21
  208. Abramovitz DL, Friedman RA, Pyle AM. 1996. Science 271:1410–13
  209. Hamm ML, Piccirilli JA. 1997. J. Org. Chem. 62:3415–20
  210. Schärer OD, Kawate T, Gallinari P, Jiricny J, Verdine GL. 1997. Proc. Natl. Acad. Sci. USA 94:4878–83
  211. Osborne SE, Ellington AD. 1997. Chem. Rev. 97:349–70
  212. Jellinek D, Green LS, Bell C, Lynott CK, Gill N. et al. 1995. Biochemistry 34:11363–72
  213. Lin Y, Nieuwlandt D, Magallanez A, Feistner B, Jayasena SD. 1996. Nucleic Acids Res. 24:3407–14
  214. Lee S-W, Sullenger BA. 1997. Nat. Biotechnol. 15:41–45
  215. Pagraitis NC, Bell C, Chang Y-F, Jennings S, Fitzwater T. et al. 1997. Nat. Biotechnol. 15:68–73
  216. Barabino SM, Sproat BS, Ryder U, Blencowe BJ, Lamond AI. 1989. EMBO J. 8:4171–78
  217. Blencowe BJ, Sproat BS, Ryder U, Barabino S, Lamond AI. 1989. Cell 59:531–39
  218. Bardwell VJ, Wickens M, Bienroth S, Keller W, Sproat BS, Lamond AI. 1991. Cell 65:125–33
  219. Froehler BC, Ricca DJ. 1992. J. Am. Chem. Soc. 114:8320–22
  220. Bulychev NV, Varaprasad CV, Dorman G, Miller JH, Eisenberg M. et al. 1996. Biochemistry 35:13147–56
  221. Burlina F, Favre A, Fourrey J-L, Thomas M. 1996. Chem. Commun.,1623–24
  222. Hancox EL, Connolly BA, Walker RT. 1993. Nucleic Acids Res. 21:3485–91
  223. Hess MT, Schwitter U, Petretta M, Giese B, Naegeli H. 1997. Biochemistry 36:2332–37
  224. Schärer OD, Ortholand J-Y, Ganesan A, Ezaz-Nikpay K, Verdine GL. 1995. J. Am. Chem. Soc. 11:6623–24
  225. Millar DP. 1996. Curr. Opin. Struct. Biol. 6:322–26
  226. Ward DC, Reich E, Stryer L. 1969. J. Biol. Chem. 244:1228–37
  227. Xu D, Evans KO, Nordlund TM. 1994. Biochemistry 33:9592–99
  228. Guest CR, Hochstrasser RA, Sowers LC, Millar DP. 1991. Biochemistry 30:3271–79
  229. Hochstrasser RA, Carver TE, Sowers LC, Millar DP. 1994. Biochemistry 33:11971–79
  230. Bloom LB, Otto MR, Eritja R, Reha-Krantz LJ, Goodman MF, Beechem JM. 1994. Biochemistry 33:7576–86
  231. Marquez LA, Reha-Krantz LJ. 1996. J. Biol. Chem. 271:28903–11
  232. Bloom LB, Otto MR, Beechem JM, Goodman MF. 1993. Biochemistry 32:11247–58
  233. Frey MW, Sowers LC, Millar DP, Benkovic SJ. 1995. Biochemistry 34:9185–92
  234. Raney KD, Sowers LC, Millar DP, Benkovic SJ. 1994. Proc. Natl. Acad. Sci. USA 91:6644–48
  235. Menger M, Tuschl T, Eckstein F, Porschke D. 1996. Biochemistry 35:14710–16
  236. Hawkins ME, Pfleiderer W, Mazumder A, Pommier YG, Balis FM. 1995. Nucleic Acids Res. 23:2872–80
  237. Wu PG, Nordlund TM, Gildea B, McLaughlin LW. 1990. Biochemistry 29:6508–14
  238. Guest CR, Hochstrasser RA, Dupuy CG, Allen DJ, Benkovic SJ, Millar DP. 1991. Biochemistry 30:8759–70
  239. Bailey M, Hagmar P, Millar DP, Davidson BE, Tong G. et al. 1995. Biochemistry 34:15802–12
  240. Allen DJ, Darke PL, Benkovic SJ. 1989. Biochemistry 28:4601–7
  241. Ozaki H, McLaughlin LW. 1992. Nucleic Acids Res. 20:5205–14
  242. Fidanza JA, McLaughlin LW. 1992. J. Org. Chem. 57:2340–46
  243. Lee LG, Connell CR, Woo SL, Cheng RD, McArdle BF. et al. 1992. Nucleic Acids Res. 20:2471–83
  244. Ju JY, Glazer AN, Mathies RA. 1996. Nucleic Acids Res. 24:1144–48
  245. Walter NG, Burke JM. 1997. RNA 3:392–404
  246. Hustedt EJ, Kirchner JJ, Spalstenstein A, Hopkins PB, Robinson BH. 1995. Biochemistry 34:4369–75
  247. Miller TR, Alley SC, Reese AW, Solomon MS, McCallister WV. et al. 1995. J. Am. Chem. Soc. 117:9377–78
  248. Thorogood H, Waters TR, Parker AW, Wharton CW, Connolly BA. 1996. Biochemistry 35:8723–33
  249. Ferentz AE, Keating TA, Verdine GL. 1993. J. Am. Chem. Soc. 115:9006–14
  250. Ferentz AE, Verdine GL. 1994. Nucleic Acids Mol. Biol. 8:14–40
  251. Allerson CR, Chen SL, Verdine GL. 1997. J. Am. Chem. Soc. 119:7423–33
  252. Wolfe SA, Ferentz AE, Grantcharova V, Churchill MEA, Verdine GL. 1995. Chem. Biol. 2:213–21
  253. Erlanson DA, Chen L, Verdine GL. 1993. J. Am. Chem. Soc. 115:12583–84
  254. Allerson CR, Verdine GL. 1995. Chem. Biol. 2:667–75
  255. Osborne SE, Völker J, Stevens SY, Breslauer KJ, Glick GD. 1996. J. Am. Chem. Soc. 118:11993–12003
  256. Goodwin JT, Osborne SE, Scholle EJ, Glick GD. 1996. J. Am. Chem. Soc. 118:5207–15
  257. Osborne SE, Cain RJ, Glick GD. 1997. J. Am. Chem. Soc. 119:1171–82
  258. Milton J, Connolly BA, Nikiforov TT, Cosstick R. 1993. J. Chem. Soc. Chem. Commun.,779–80
  259. Cowart M, Gibson KJ, Allen DJ, Benkovic SJ. 1989. Biochemistry 28:1975–83
  260. Cowart M, Benkovic SJ. 1991. Biochemistry 30:788–96
  261. Sigurdsson STh, Tuschl T, Eckstein F. 1995. RNA 1:575–83
  262. Sigurdsson STh, Eckstein F. 1996. Nucleic Acids. Res. 24:3129–33
  263. Deleted in proof
  264. Cohen SB, Cech TR. 1997. J. Am. Chem. Soc. 119:6259–68
  265. Behlen LS, Sampson JR, Uhlenbeck OC. 1992. Nucleic Acids Res. 20:4055–59
  266. Burke JM, Butcher SE, Sargueil B. 1996. Nucleic Acids Mol. Biol. 10:129–43
  267. Nikiforov TT, Connolly BA. 1992. Nucleic Acids Res. 20:1209–14
  268. Favre A, Michelson AM, Yaniv M. 1971. J. Mol. Biol. 58:367–79
  269. Dontsova O, Kopylov A, Brimacombe R. 1991. EMBO J. 10:2613–20
  270. McGregor A, Rao MV, Duckworth G, Stockley PG, Connolly BA. 1996. Nucleic Acids Res. 24:3173–80
  271. Sontheimer EJ, Steitz JA. 1993. Science 262:1989–96
  272. Mishima Y, Steitz JA. 1995. EMBO J. 14:2679–87
  273. Yu Y-T, Steitz JA. 1997. Proc. Natl. Acad. Sci. USA 94:6030–35
  274. Favre A, Fourrey J-L. 1995. Acc. Chem. Res. 28:375–82
  275. Gott JM, Willis MC, Koch TH, Uhlenbeck OC. 1991. Biochemistry 30:6290–95
  276. Willis MC, Hicke BJ, Uhlenbeck OC, Cech TR, Koch TH. 1993. Science 262:1255–57
  277. Hicke BJ, Willis MC, Koch TH, Cech TR. 1994. Biochemistry 33:3364–73
  278. Langer PR, Waldrop AA, Ward DC. 1981. Proc. Natl. Acad. Sci. USA 78:6633–37
  279. Catalano CE, Allen DJ, Benkovic SJ. 1990. Biochemistry 29:3612–21
  280. Capson TL, Benkovic SJ, Nossal NG. 1991. Cell 65:249–58
  281. Reems JA, Wood S, McHenry CS. 1995. J. Biol. Chem. 270:5606–13
  282. Sergiev PV, Lavrik IN, Wlasoff VA, Dokudovskaya SS, Dontsova OA. et al. 1997. RNA 3:464–75
  283. Jayaram B, Haley BE. 1994. J. Biol. Chem. 269:3233–42
  284. Chavan A, Nemoto Y, Narumiya S, Kozaki S, Haley BE. 1992. J. Biol. Chem. 267:14866–70
  285. Wower J, Hixson SS, Zimmermann RA. 1989. Proc. Natl. Acad. Sci. USA 86:5232–36
  286. Evans RK, Haley BE. 1987. Biochemistry 26:269–76
  287. He BK, Riggs DL, Hanna MM. 1995. Nucleic Acids Res. 23:1231–38
  288. Harris ME, Nolan JM, Malhotra A, Brown JW, Harvey SC, Pace NR. 1994. EMBO J. 13:3953–63
  289. Harris ME, Kazantsev AV, Chen J-L, Pace NR. 1997. RNA 3:561–76
  290. Wang J-F, Downs WD, Cech TR. 1993. Science 260:504–8
  291. Manchanda R, Dunham SU, Lippard SJ. 1996. J. Am. Chem. Soc. 118:5144–45
  292. Boudvillain M, Guerin M, Dalbies R, Saison-Behmoaras T, Leng M. 1997. Biochemistry 36:2925–31
/content/journals/10.1146/annurev.biochem.67.1.99
Loading
MODIFIED OLIGONUCLEOTIDES: Synthesis and Strategy for Users
Annual Review of Biochemistry 67, 99 (1998); https://doi.org/10.1146/annurev.biochem.67.1.99
/content/journals/10.1146/annurev.biochem.67.1.99
/content/journals/10.1146/annurev.biochem.67.1.99
Loading

Data & Media loading...

  • Article Type: Introduction

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error