Crystal structure of homo-DNA and nature's choice of pentose over hexose in the genetic system

Journal of the American Chemical Society

Volumn 128, Issue 33, 2006, Pages 10847-10856

  Egli, Martin ^a   Pallan, Pradeep S ^a   Pattanayek, Rekha ^a   Wilds, Christopher J ^a,b   Lubini, Paolo ^c   Minasov, George ^d   Dobler, Max ^e   Leumann, Christian J ^f   Eschenmoser, Albert ^g,h  

^a VANDERBILT UNIVERSITY   (United States)

^b Gina Cody School of Engineering and Computer Science   (Canada)

^c Alta Scuola Pedagogica   (Switzerland)

^d NORTHWESTERN UNIVERSITY   (United States)

^e Biographics Laboratory 3R   (Switzerland)

^f UNIVERSITY OF BERN   (Switzerland)

^g SCRIPPS RESEARCH INSTITUTE   (United States)

^h ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; DNA; GENETIC ENGINEERING; MOLECULAR STRUCTURE; NUCLEIC ACIDS; PHOSPHATES; PHYSICAL PROPERTIES;

GENETIC SYSTEM; HEXAPYRANOSYL; HEXOSE-PHOSPHATE; NUCLEOTIDES;

PROTEINS;

DNA; HEXOSE; PENTOSE; PHOSPHOROTHIOIC ACID DERIVATIVE; SELENIUM DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

DNA; HEXOSES; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; PENTOSES;

EID: 33747792737     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062548x     Document Type: Article

References (46)

1. Eschenmoser, A.; Kisakürek, M. V. Helv. Chim. Acta 1996, 79, 1249-1259.
2. Eschenmoser, A. Science 1999, 284, 2118-2124.
3. Pitsch, S.; Krishnamurthy, R.; Bolli, M.; Wendeborn, S.; Holzner, A.; Minton, M.; Lesueur, C.; Schlönvogt, I.; Jaun, B.; Eschenmoser, A. Helv. Chim. Acta 1995, 78, 1621-1635.
4. Beier, M.; Reck, F.; Wagner, T.; Krishnamurthy, R.; Eschenmoser, A. Science 1999, 283, 699-703.
5. Jungmann, O.; Wippo, H.; Stanek, M.; Huynh, H. K.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 1999, 1, 1527-1530.
6. Reck, F.; Wippo, H.; Kudick, R.; Bolli, M.; Ceulemans, G.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 1999, 1, 1531-1534.
7. Schöning, K. U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 290, 1347-1351.
8. Eschenmoser, A.; Loewenthal, E. Chem. Soc. Rev. 1992, 21, 1-16.
9. Eschenmoser, A. In 40 years of the DNA double helix; Proceedings of the Robert A. Welch Foundation Conference on Chemical Research; Houston, TX, Oct 25 and 26, 1993; R. A. Welch Foundation: Houston, TX, 1993; pp 201-235.
10. Böhringer, M.; Roth, H.-J.; Hunziker, J.; Göbel, M.; Krishnan, R.; Giger, A.; Schweizer, B.; Schreiber, J.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1992, 75, 1416-1477.
11. Hunziker, J.; Roth, H.-J.; Böhringer, M.; Giger, A.; Diedrichsen, U.; Göbel, M.; Krishnan, R.; Jaun, B.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 259-352.
12. Eschenmoser, A.; Dobler, M. Helv. Chim. Acta 1992, 75, 218-259.
13. Groebke, K.; Hunziker, J.; Faser, W.; Peng, L.; Diedrichsen, U.; Zimmermann, K.; Holzner, A.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1998, 81, 375-474.
14. Froeyen, M.; Lescrinier, E.; Kerremans, L.; Rosemeyer, H.; Seela, F.; Verbeure, B.; Lagoja, I.; Rozenski, J.; Van Aerschot, A.; Busson, R.; Herdewijn, P. Chem.-Eur. J. 2001, 7, 5183-5194.
15. Declercq, R.; Van Aerschot, A.; Read, R. J.; Herdewijn, P.; Van Meervelt, L. J. Am. Chem. Soc. 2002, 124, 928-933.
16. Otting, G.; Billeter, M.; Wüthrich, K.; Roth, H.-J.; Leumann, C.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 2701-2756.
17. Lescrinier, E.; Froeyen, M.; Herdewijn, P. Nucleic Acids Res. 2003, 3l, 2975-2989.
18. Wilds, C. J.; Pattanayek, R.; Pan, C.; Wawrzak, Z.; Egli, M. J. Am. Chem. Soc. 2002, 124, 14910-14916.
19. Brünger A. T.; Adams P. D.; Clore G. M.; DeLano W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Acta Crystallogr., Sect. D 1998, 54, 905-921.
20. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
21. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D 1997, 53, 240-255.
22. Rich, A. Nat. Struct. Biol. 2003, 10, 247-249.
23. Wang, A. H.-J.; Quigley, G. J.; Kolpak, F. J.; Crawford, J. L.; van Boom, J. H.; van der Marel, G.; Rich, A. Nature 1979, 282, 680-686.
24. Han, G. W.; Kopka, M. L.; Langs, D.; Sawaya, M. R.; Dickerson, R. E. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9214-9219.
25. Dickerson, R. E. Nucleic Acids Res. 1989, 17, 1797-1803.
26. Newman, W. N.; Sproull, R. F. Principles of Interactive Computer Graphics, 2nd ed.; McGraw-Hill: New York, 1979; Chapter 21.
27. Germann, M. W.; Kalisch, B. W.; van de Sande, J. H. Biochemistry 1988, 27, 8302-8306.
28. Otto, C.; Thomas, G. A.; Jovin, T. M.; Peticolas, W. L. Biochemistry 1991, 30, 3062-3069.
29. Guga, P.; Maciaczek, A.; Stec, W. J. Org. Lett. 2005, 7, 3901-3904.
30. Yagil, G.; Sussman, J. L. EMBO J. 1986, 5, 1719-1725.
31. Pitsch, S.; Wendeborn, S.; Jaun, B.; Eschenmoser, A. Helv. Chim. Acta 1993, 76, 2161-2183.
32. Schlönvogt, I.; Pitsch, S.; Lesueur, C.; Eschenmoser, A.; Jaun, B.; Wolf, R. M. Helv. Chim. Acta 1996, 79, 2316-2345.
33. Gehring, K.; Leroy, J.-L.; Guéron, M. A. Nature 1993, 363, 561-565.
34. Pitsch, S.; Krishnamurthy, R.; Bolli, M.; Wendeborn, S.; Holzner, A.; Minton, M.; Lesueur, C.; Schlönvogt, I.; Jaun, B.; Eschenmoser, A. Helv. Chim. Acta 1995, 78, 1621-1635.
35. Bolli, M.; Micura, R.; Eschenmoser, A. Chem. Biol. 1997, 4, 309-320.
36. Micura, R.; Bolli, M.; Windhab, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 870-873.
37. Petersheim, M.; Turner, D. H. Biochemistry 1983, 22, 256-263.
38. Freier, S. M.; Burger, B. J.; Alkema, D.; Neilson, T.; Turner, D. H. Biochemistry 1983, 22, 6198-6206.
39. Oberhuber, M.; Joyce, G. F. Angew. Chem., Int. Ed. 2005, 44, 7580-7583.
40. Iyer, R. P.; Egan, W.; Regahn, J. B.; Beaucage, S. J. Am. Chem. Soc. 1990, 112, 1253-1254.
41. Cambillau C.; Roussel A. Turbo Frodo, version OpenGL.1; Université Aix-Marseille II: Marseille, France, 1997.
42. The CCP4 suite: Programs for protein crystallography. Collaborative computing project, number 4. Acta Crystallogr., Seer. D 1994, 50, 760-763.
43. Murshudov, G. N.; Vagin, A. A.; Lebedev, A.; Wilson, K. S.; Dodson, E. J. Acta Crystallogr., Sect. D 1999, 55, 247-255.
44. Winn, M. D.; Isupov, M. N.; Murshudov, G. N. Acta Crystallogr., Sect. D 2001, 57, 122-133.
45. Lavery, R.; Sklenar, H. J. Biomol. Struct. Dyn. 1989, 6, 655-667.
46. Egli, M.; Lubini, P.; Pallan, P. S. Chem. Soc. Rev. 2006, 35, in press.