Conformation, optical properties, and absolute configuration of 2′,3′-isopropylideneadenosines: Theoretical vs. experimental study

Journal of Molecular Structure

Volumn 1004, Issue 1-3, 2011, Pages 303-312

  Ivanova, Bojidarka ^a   Spiteller, Michael ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

2 ,3 Isopropylideneadenosines; Quantum chemistry; Spectroscopy

Indexed keywords

CHLORINE COMPOUNDS; CIRCULAR DICHROISM SPECTROSCOPY; CONFORMATIONS; DESIGN FOR TESTABILITY; DICHROISM; MASS SPECTROMETRY; MOLECULES; QUANTUM CHEMISTRY; SINGLE CRYSTALS; SPECTROSCOPY; STEREOCHEMISTRY; X RAY DIFFRACTION;

ABSOLUTE CONFIGURATION; CONFORMATIONAL ANALYSIS; ELECTRONIC ABSORPTION; ELECTRONIC CIRCULAR DICHROISM; INTERMOLECULAR INTERACTIONS; MASS SPECTROMETRIC IMAGING; SINGLE CRYSTAL X-RAY DIFFRACTION; STRUCTURE-BASED DESIGNS;

DENSITY FUNCTIONAL THEORY;

EID: 80053574587     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2011.08.027     Document Type: Article

References (191)

1. E. Meggers, and L. Zhang Accts. Chem. Res. 43 2010 1092
2. W. Jorgensen Accts. Chem. Res. 42 2009 724
3. D. Zhang, H. Song, and Y. Qin Accts. Chem. Res. 2011 10.1021/ar200004w
4. E. Stellwagen, and S. Lippard Accts. Chem. Res. 12 1979 204
5. S. Lippard Accts. Chem. Res. 11 1978 211
6. M. Cohn Accts. Chem. Res. 15 1982 326
7. K. Burgess, and D. Cook Chem. Rev. 100 2000 2047
8. G. Romeo, U. Chiacchio, A. Corsaro, and P. Merino Chem. Rev. 110 2010 3337
9. P. Li, Z. Sergueeva, M. Dobrikov, and B. Shaw Chem. Rev. 107 2007 4746
10. J. Sponer, J. Leszczynski, and P. Hobza Biopolymers 61 2001 3
11. N. Seeman Nature 421 2003 427
12. L. Zhang, A. Peritz, and E. Meggers J. Am. Chem. Soc. 127 2005 4174
13. K. Schöning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, and A. Eschenmoser Science 290 2001 1347
14. M. Schlegel, X. Xie, L. Zhang, and E. Meggers Angew. Chem., Int. Ed. 48 2009 960
15. L. Orgel Crit. Rev. Biochem. Mol. Biol. 39 2004 99
16. G. Cooper, N. Kimmich, W. Belisle, J. Sarinana, K. Brabham, and L. Garrel Nature 414 2001 879
17. J. Chen, X. Cai, and J. Szostak J. Am. Chem. Soc. 131 2008 2119
18. S. Sprang, D. Rohrer, and M. Sundaralingam Acta. Cryst. B34 1978 2803
19. J. Secrist III, and N. Leonard J. Am. Chem. Soc. 94 1972 1702
20. S. Verma, S. Mishra, and J. Kumar Accts. Chem. Res. 43 2010 79
21. H. Sigel Chem. Soc. Rev. 22 1993 255
22. B. Lippert Coord. Chem. Rev. 200 2000 487
23. R. Martin Accts. Chem. Res. 18 1985 32
24. L. Prizant, M. Olivier, R. Rivest, and A. Beauchamp J. Am. Chem. Soc. 101 1979 2765
25. C. Meiser, B. Song, E. Freisinger, M. Peilert, H. Sigel, and B. Lippert Chem. Eur. J. 3 1997 388
26. C. Purohit, A. Mishra, and S. Verma Inorg. Chem. 46 2007 8493
27. J. Lehn Science 295 2002 2400
28. G. Whitesides, and B. Grzybowski Science 295 2002 2418
29. S. Li, B. Northrop, Q. Yuan, L. Wan, and P. Stang Accts. Chem. Res. 42 2009 249
30. M. Ruben, J. Lehn, and P. Muller Chem. Soc. Rev. 35 2006 1056
31. J. Barth, G. Costantini, and K. Kern Nature 437 2005 671
32. N. Williams, B. Takaasaki, M. Wall, and J. Chin Accts. Chem. Res. 32 1999 485
33. M. Ruben, J. Rojo, F. Romero-Salguero, L. Uppadine, and J. Lehn Angew. Chem., Int. Ed. 28 2004 3644
34. B. Bouidaffa, P. Cloutier, D. Hunting, M. Huels, and L. Sanche Science 287 2000 1658
35. C. Perigaud, G. Gosselin, and J. Imbach Nucleosid, Nucleot. 11 1992 903
36. C. Wagner, V. Iyer, and E. McIntee J. Med. Res. Rev. 20 2000 417
37. G. Koomen J. Recl. Trav. Chim. Pays-Bas 112 1993 51
38. X. Tan, C. Chu, and F. Boudinot Adv. Drug Deliv. Rev. 39 1999 117
39. C. Galmarini Electron. J. Oncol. 1 2002 22
40. D. Huryn, and M. Okabe Chem. Rev. 92 1992 1745
41. C. Meier Synlett 3 1998 233
42. Q. Wu, and S. Simons Synthesis 10 2004 1533
43. M. Meldgaard, and J. Wengel J. Chem. Soc., Perkin Trans. 1 21 2000 539
44. E. El Ashry, and N. Rashed Curr. Org. Chem. 4 2000 609
45. E. Ichikawa, and K. Kato Curr. Med. Chem. 8 2001 385
46. E. Ichikawa, and K. Kato Synthesis 1 2002 1
47. H. Gao, and A. Mitra Synthesis 3 2000 329
48. D. Huryn, and M. Okabe Chem. Rev. 92 1992 1745
49. R. Lyngdoh, and H. Schaefer III Accts. Chem. Res. 42 2009 563
50. X. Li, M. Sevilla, and L. Sanche J. Am. Chem. Soc. 125 2003 13668
51. Y. Zheng, P. Cloutier, D. Hunting, J. Wagner, and L. Sanche J. Am. Chem. Soc. 126 2004 1002
52. J. Rienstra-Kiracofe, G. Tschumper, H. Schaefer III, S. Nandi, and G. Ellison Chem. Rev. 102 2002 231
53. A. Reed, L. Curtiss, and F. Weinhold Chem. Rev. 88 1988 899
54. M. Cossi, V. Barone, R. Cammi, and J. Tomasi J. Chem. Phys. Lett. 255 1996 327
55. N. Russo, M. Toscano, and A. Grand J. Comput. Chem. 21 2000 1243
56. S. Wesolowski, M. Leininger, P. Pentchev, and H. Schaefer III J. Am. Chem. Soc. 123 2001 4023
57. S. Kim, and H. Schaefer III J. Chem. Phys. 125 2006 144305
58. S. Kim, and H. Schaefer III J. Chem. Phys. 126 2007 64301
59. N. Richardson, J. Gu, S. Wang, Y. Xie, and H. Schaefer III J. Am. Chem. Soc. 124 2004 4404
60. S. Stokes, X. Li, A. Grubisic, Y. Ko, and K. Bowen J. Chem. Phys. 127 2007 084321
61. J. Gu, Y. Xie, and H. Schaefer III J. Am. Chem. Soc. 127 2005 1053
62. Y. Zheng, P. Cloutier, D. Hunting, L. Sanche, and J. Wagner J. Am. Chem. Soc. 125 2005 16592
63. J. Simons Acc. Chem. Res. 39 2006 772
64. J. Gu, Y. Xie, and H. Schaefer III J. Am. Chem. Soc. 128 2006 1250
65. N. Richardson, S. Wesolowski, and H. Schaefer III J. Phys. Chem. B 107 2003 848
66. S. Kim, and H. Schaefer III J. Phys. Chem. A 111 2007 10381
67. J. Gu, Y. Xie, and H. Schaefer III J. Chem. Phys. 127 2007 155107
68. S. Kusari, and S. Zühlke M. Spiteller Phytoche. Anal. 22 2011 128
69. M. Awouafack, P. Spiteller, M. Lamshöft, S. Kusari, B. Ivanova, P. Tane, and M. Spiteller J. Nat. Prod. 74 2011 272
70. M. Awouafack, S. Kusari, M. Lamshöft, D. Ngamga, P. Tane, and M. Spiteller Planta Med. 76 2010 640
71. B. Kindler, H. Krämer, S. Nies, P. Gradicsky, G. Haase, P. Mayser, M. Spiteller, and P. Spiteller Eur. J. Org. Chem. 11 2010 2084
72. S. Kusari, S. Zühlke, T. Borsch, and M. Spiteller Phytochem. 70 2009 1222
73. H. Zhang, I. Oppel, M. Spiteller, K. Günther, G. Böhmler, and S. Zühlke Chirality 21 2009 271
74. S. Kusari, S. Zühlke, and M. Spiteller J. Nat. Prod. 2011 10.1021/np1008398
75. S. Kusari, S. Zühlke, and M. Spiteller J. Nat. Prod. 72 2009 2
76. S. Kusari, S. Zühlke, J. Košuth, E. Cellárová, and M. Spiteller J. Nat. Prod. 72 2009 825
77. S. Kusari, M. Lamshöft, S. Zühlke, and M. Spiteller J. Nat. Prod. 71 2008 159
78. P. Wender, and B. Miller Nature 460 2009 197
79. P. Wender, V. Verma, T. Paxton, and T. Pillow Accts. Chem. Res. 41 2008 40
80. H. Mackay, and C. Twelves Endocr.-Relat. Cancer 10 2003 389
81. P. Wender, and C. Zercher J. Am. Chem. Soc. 113 1991 2311
82. S. Kusari, and M. Spiteller Nat. Prod. Rep. 28 2011 1203
83. S. Grimme, and F. Neese J. Chem. Phys. 127 2007 154116
84. Y. Zhao, N. Schultz, and D. Truhlar J. Chem. Theory Comput. 2 2006 364
85. P. Stephens, J. Pan, F. Devlin, and J. Cheeseman J. Nat. Prod. 71 2008 285
86. P. Stephens, D. McCann, F. Devlin, and A. Smith III J. Nat. Prod. 69 2006 1055
87. P. Stephens, D. McCann, J. Cheeseman, and M. Frisch Chirality 17 2005 S52
88. P. Stephens, F. Devlir, J. Cheeseman, and M. Frisch J. Phys. Chem. A 105 2001 5356
89. B. Mennucci, J. Tomasi, R. Cammi, J. Cheeseman, M. Frisch, F. Devlin, S. Gabriel, and P. Stephens J. Phys. Chem. A 106 2002 6102
90. P. Stephens, F. Devlin, J. Cheeseman, M. Frisch, and C. Rosini Org. Lett. 4 2002 4595
91. P. Polavarapu, and D. Chakraborty J. Am. Chem. Soc. 120 1998 6160
92. P. Polavarapu, and C. Zhao Chem. Phys. Lett. 296 1998 105
93. S. Grimme, A. Bahlmann, and G. Haufe Chirality 14 2002 793
94. S. Grimme, F. Furche, and S. Ahlrichs Chem. Phys. Lett. 361 2002 321
95. J. Autschbach, S. Patchkovskii, T. Ziegler, and S. van Gisbergen Baerends J. Chem. Phys. 117 2002 581
96. D. Beratan, R. Kondru, and P. Wipf ACS Symp. Ser. 810 2002 104
97. S. Grimme Chem. Phys. Lett. 339 2001 380
98. S. Grimme, F. Furche, and R. Ahlrichs Chem. Phys. Lett. 361 2002 321
99. C. Wachsmann, E. Weber, A. Sobanski, F. Vogtle, and S. Grimme J. Am. Chem. Soc. 122 2000 1717
100. L. Polavarapu Angew. Chem., Int. Ed. 41 2002 4544
101. Y. Wang, G. Raabe, C. Repges, and J. Fleischhauer Int. J. Quant. Chem. 93 2003 265
102. P. Polavarapu Chirality 14 2002 768
103. P. Stephens, J. Devlin, M. Cheeseman, and M. Frisch Chirality 15 2003 S57
104. Y. Zhao, and D. Truhlar Accts. Chem. Res. 41 2008 157
105. N. Schultz, Y. Zhao, and D. Truhlar J. Comput. Chem. 29 2008 185
106. Y. Zhao, and D. Truhlar Theor. Chem. Acc. 120 2008 215
107. M. Caricato, T. Vreven, G. Trucks, and M. Frisch Chem. Theor. Comp. 7 2011 180
108. M. Caricato, G. Trucks, M. Frisch, and K. Wiberg J. Chem. Theor. Comp. 6 2010 370
109. R. Improta, V. Barone, G. Scalmani, and M. Frisch Chem. Phys. 125 2006 054103
110. R. Improta, G. Scalmani, M. Frisch, and V. Barone Chem. Phys. 127 2007 074504
111. F. De Proft, and P. Geerlings Chem. Rev. 101 2001 1451
112. F. Santoro, V. Barone, A. Lami, and R. Improta Phys. Chem. Chem. Phys. 12 2010 493
113. V. Karunakaran, K. Kleinermanns, R. Improta, and S. Kovalenko J. Am. Chem. Soc. 131 2009 5839
114. D. Crawford Theor. Chem. Acc. 115 2006 227
115. B. Koleva, T. Kolev, and M. Spiteller Biopolymers 83 2006 498
116. B. Koleva, T. Kolev, and M. Spiteller Spectrochim. Acta 68 2007 1187
117. T. Kolev, B. Koleva, and M. Spiteller Amino Acids 33 2007 719
118. T. Kolev, M. Spiteller, and B. Koleva Amino Acids 38 2010 45
119. B. Ivanova Spectrochim. Acta 64 2006 931
120. M. Fu1lscher, L. Serrano-Andres, and B. Roos J. Am. Chem. Soc. 119 1997 6168
121. M. Fülscher, and B. Roos J. Am. Chem. Soc. 117 1995 2089
122. F. Lorentzon, M. Fülscher, and B. Roos J. Am. Chem. Soc. 117 1995 9265
123. L. Clark, G. Peschel, and I. Tinoco Jr. J. Phys. Chem. 69 1965 3615
124. C. Sprecher, and W. Johnson Jr. Biopolymers 16 1977 2243
125. W. Brunner, and M. Maestre Biopolymers 14 1975 555
126. L. Clark J. Phys. Chem. 94 1990 2873
127. T. Yamada, and H. Fukutome Biopolymers 6 1968 43
128. S. Mishra, M. Shukla, and P. Mishra Spectrochim. Acta 56A 2000 1355
129. D. Cornett, M. Reyzer, P. Chaurand, and R. Caprioli Nat. Meth. 4 2007 828
130. T. Sinha, S. Khatib-Shahidi, T. Yankeelov, K. Mapara, M. Ehtesham, D. Cornett, B. Dawant, R. Caprioli, and J. Gore Nat. Meth. 5 2008 57
131. M. Glinski, and W. Weckwerth Mass Spectrom. Rev. 25 2006 173
132. M. Claydon, S. Davey, V. Jones, and D. Gordon Nat. Biotech. 14 1996 1584
133. M. Pacholski, and N. Winograd Chem. Rev. 99 1999 2977
134. Y. Li, B. Shrestha, and A. Vertes Anal. Chem. 80 2008 407
135. K. Burnum, S. Frappier, and R. Caprioli Annu. Rev. Anal. Chem. 1 2008 689
136. R. Cole Electrospray and MALDI Mass Spectrometry 2010 Wiley
137. S. Rubakhin, and J. Sweedler Mass Spectrometry Imaging 2010 Springer (Humana Press)
138. B. Kaletas, I. Van der Wiel, J. Stauber, C. Guzel, J. Cros, T. Luider, and T. Heeren Proteomics 9 2009 2622
139. J. Edwards, and R. Kennedy Anal. Chem. 77 2005 2201
140. Y. Liu, X. Sun, and B. Guo Rapid Commun. Mass Spectrom. 17 2003 2354
141. E. Romanova, S. Rubakhin, and J. Sweedler Anal. Chem. 80 2008 3379
142. X. Chen, J. Carroll, and R. Beavis J. Am. Soc. Mass Spectrom. 9 1998 885
143. V. Karbach, and R. Knochenmuss Rapid. Commun. Mass Spectrom. 12 1998 968
144. J. Ireland, and P. Wyatt Adv. Phys. Org. Chem. 12 1976 131
145. M. Gimon, L. Preston, T. Solouki, M. White, and D. Russell Org. Mass Spectrom. 27 1992 827
146. H. Ludemann, F. Hillenkamp, and R. Redmond J. Phys. Chem. A 104 2000 3884
147. R. Krüger, A. Pfenninger, I. Fournier, M. Glückmann, and M. Karas Anal. Chem. 73 2001 5812
148. M. Karas, M. Glückmann, and J. Schafer J. Mass Spectrom. 35 2000 1
149. P. Setz, and R. Knochenmuss J. Phys. Chem. A 109 2005 4030
150. R. Knochenmuss J. Mass Spectrom. 37 2002 867
151. K. Strupat, V. Kovtoun, H. Bui, R. Viner, G. Stafford, and S. Horning J. Am. Soc. Mass. Spectrom. 20 2009 1451
152. G.M. Sheldrick Acta Cryst. A64 2008 112
153. G.M. Sheldrick Acta. Cryst. D66 2010 479
154. G.M. Sheldrick Acta Cryst. A46 1990 467
155. R.H. Blessing Acta Cryst. A51 1995 33
156. A. Spek J.Appl.Cryst. 36 2003 7
157. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.3, Gaussian Inc., Pittsburgh, PA, 1998.
158. Dalton 2.0 program package, < http://www.kjemi.uio.no/software/dalton/ dalton.html >.
159. GausView03, < http://www.softwarecientifico.com/paginas/gaussian.htm >.
160. F. Jensen Introduction to Computational Chemistry 1999 Wiley New York
161. M. Head-Gordon, J. Pople, and M. Frisch Chem. Phys. Lett. 153 1988 503
162. W. Stevens, M. Krauss, H. Basch, and P. Jansen Can. J. Chem. 70 1992 612
163. W. Hehre, L. Radom, P. Schleyer, and J. Pople Ab Initio Molecular Orbital Theory 1986 Wiley New York
164. D. Woon, and T. Dunning J. Chem. Phys. 98 1993 1358
165. J. Foresman, M. Head-Gordon, J. Pople, and M. Frisch J. Phys. Chem. 96 1992 135
166. R. Stratmann, G. Scuseria, and M. Frisch J. Chem. Phys. 109 1998 8218
167. S. van Gisbergen, J. Groeneveld, J. Snijders, and E. Baerends J. Phys. Chem. A 103A 1999 6835
168. A. Becke J. Chem. Phys. 96 1992 2155
169. R. Pappalardo, M. Reguero, M. Robb, and M. Frisch Chem. Phys. Lett. 212 1993 12
170. T. Truong, and E. Stefanovich Chem. Phys. Lett. 240 1995 253
171. J. Foresman, T. Keith, K. Wiberg, J. Snoonian, and M. Frisch J. Phys. Chem. 100 1996 16098
172. M. Svensson, S. Humbel, R. Froese, T. Matsubara, S. Sieber, and K. Morokuma J. Phys. Chem. 100 1996 19357
173. http://de.openoffice.org/.
174. C. Kelley Iterative Methods for Optimization vol. 18 1999 SIAM Frontiers in Applied Mathematics
175. K. Madsen, H. Nielsen, and O. Tingleff Informatics and Mathematical Modelling second ed. 2004 DTU Press
176. A. Yildiz, and P. Selvin Accts. Chem. Res. 38 2005 574
177. D. Marquardt J. Soc. Ind. Appl. Math. 11 1963 431
178. S. Savitzky, and M. Golay Anal. Chem. 36 1964 1627
179. G. Steiner Anal. Chem. 44 1972 1906
180. M. Madden Anal. Chem. 50 1978 1383
181. P. Wilson, and S. Polo J. Opt. Soc. Am. 71 1981 599
182. C. Brown, P. Lynch, R. Obremski, and D. Lavery Anal. Chem. 54 1982 1472
183. D. Haaland, and R. Easterling Appl. Spectrosc. 34 1980 539
184. H. Haaland, and R. Easterling Appl. Spectrosc. 36 1982 665
185. D. Haaland, R. Easterling, and D. Vopicka Appl. Spectrosc. 39 1985 73
186. P. Griffiths, and G. Pariente TrAC: Trends Anal. Chem. 5 1986 209
187. B. Ivanova, and M. Spiteller J. Phys. Chem. 114A 2010 5099
188. B. Ivanova, and M. Spiteller Cryst. Growth. Des. 10 2010 2470
189. B. Ivanova, and M. Spiteller Biopolymers 93 2010 727
190. M. Lamshoft, B. Ivanova, and M. Spiteller Talanta 2011 10.1016/j.talanta.2011.08.008
191. B. Ivanova, and M. Spiteller J. Mol. Struct. 2011 10.1016/j.molstruc. 2011.06.043