Synthesis of oligonucleotides with 3′-terminal 5-(3- acylamidopropargyl)-3′-amino-2′,3′-dideoxyuridine residues and their reactivity in single-nucleotide steps of chemical replication

Journal of Organic Chemistry

Volumn 71, Issue 3, 2006, Pages 1060-1067

  Baumhof, Patrick ^a   Griesang, Niels ^a   Bächle, Michael ^a   Richert, Clemens ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DNA; OPTIMIZATION; ORGANIC ACIDS; SOLVENTS; SYNTHESIS (CHEMICAL);

5-(3-ACYLAMIDOPROPARGYL)-3′; DIDEOXYURIDINE RESIDUES; PHOSPHORAMIDITE; SINGLE-NUCLEOTIDE STEPS;

OLIGOMERS;

2' DEOXYNUCLEOSIDE; 2',3' DIDEOXY 3' TRIFLUOROACETAMIDO 5 IODOURIDINE 5 PHOSPHORAMIDITE; 4 PYRENYLBUTYRIC ACID; 5 (3 ACYLAMIDOPROPARGYL) 3' AMINO 2',3' DIDEOXYURIDINE; 7 AZABENZOTRIAZOLE; ALKYNYL GROUP; AMINE; ANTHRAQUINONE; BENZOTRIAZOLE DERIVATIVE; BUTYRIC ACID; DEOXYURIDINE; N TRITYLPROPARGYLAMINE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DEIODINATION; DNA SYNTHESIS; DNA TEMPLATE; GENOTYPE; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; HYDROLYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OLIGOMERIZATION; RING OPENING; SCALE UP; SINGLE NUCLEOTIDE POLYMORPHISM; SONOGASHIRA REACTION; STAUDINGER REACTION;

BASE SEQUENCE; DEOXYURIDINE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 32144445388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052097j     Document Type: Article

References (66)

1. Voet, D.; Voet, J. G.; Pratt, C. W. Fundamentals of Biochemistry; J. Wiley & Sons: New York. 1999.
2. Sulston, J.; Lohrmann, R.; Orgel, L. E.; Miles, H. T. Proc. Natl. Acad. Sci. U.S.A. 1968, 59, 726-733.
3. Kozlov, I. A.; Orgel, L. E. Mol. Biol. 2000, 34, 781-789.
4. Hey, M.; Hartel, C.; Göbel, M. W. Helv. Chim. Acta 2003, 86, 844-854.
5. Koppitz, M.; Nielsen, P. E.; Orgel, L. E. J. Am. Chem. Soc. 1998, 120, 4563-4569.
6. Kozlov, I. A.; Politis, P. K.; Pitsch, S.; Herdewijn, P.; Orgel, L. E. J. Am. Chem. Soc. 1999, 121, 1108-1109.
7. Wu, X.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 2002, 4, 1283-1286.
8. Chaput, J. C.; Switzer, C. J. Am. Chem. Soc. 2000, 122, 12866-12867.
9. Gryaznov, S. M.; Letsinger, R. L. J. Am. Chem. Soc. 1993, 115, 3808-3809.
10. Gryaznov, S. M.; Schultz, R.; Chaturvedi, S. K.; Letsinger, R. L. Nucleic Acids Res. 1994, 22, 2366-2369.
11. Sando, S.; Kool, E. T. J. Am. Chem. Soc. 2002, 124, 9686-9687.
12. Sando, S.; Abe, H.; Kool, E. T. J. Am. Chem. Soc. 2004, 126, 1081-1087.
13. Ficht, S.; Mattes, A.; Seitz, O. J. Am. Chem. Soc. 2004, 126, 9970-9981.
14. Zielinski, W. S.; Orgel, L. E. Nature 1987, 327, 346-347.
15. (b) Sievers, D.; von Kiedrowski, G. Nature 1994, 369, 221-224.
16. (c) Li, T.; Nicolaou, K. C. Nature 1994, 369, 218-221.
17. Lohrmann, R.; Orgel, L. E. Nature 1976, 261, 342-344.
18. Zielinski, W. S.; Orgel, L. E. Nucleic Acids Res. 1987, 15, 1699-1715.
19. Kanavarioti, A.; Stronach, M. W.; Keiner, R. J.; Hurley, T. B. J. Org. Chem. 1995, 60, 632-637.
20. Inoue, T.; Orgel, L. E. J. Am. Chem. Soc. 1981, 103, 7666-7667.
21. (b) Joyce, G. F.; Inoue, T.; Orgel, L. E. J. Mol. Biol. 1984, 176, 279-306.
22. (c) Kozlov, I. A.; Orgel, L. E. Mol. Biol. 2000, 34, 781-789.
23. Hagenbuch, P.; Kervio, E.; Hochgesand, A.; Plutowski, U.; Richert, C. Angew. Chem. 2005, 117, 6746-6750;
24. Angew. Chem., Int. Ed. Engl. 2005, 44, 6588-6592.
25. Rojas Stütz, J. A.; Richert, C. J. Am. Chem. Soc. 2001, 123, 12718-12719.
26. Tost, J.; Gut, I. G. Clin. Biochem. 2005, 38, 335-350.
27. Stoerker, J.; Mayo, J.; Tetzlaff, C. N.; Sarracino, D. A.; Schwope, I.; Richert, C. Nat. Biotechnol. 2000, 18, 1213-1216.
28. Tang, K.; Fu, D.-J.; Julien, D.; Braun, A.; Cantor, C. E. Köster, H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10016-10020.
29. Wagner, R. W.; Matteucci, M. D.; Lewis, J. G.; Gutierrez, A. J.; Moulds, C.; Froehler, B. C. Science 1993, 260, 1510-1513.
30. Chaput, J. C.; Sinha, S.; Switzer, C. Chem. Commun. 2002, 1568-1569.
31. Connors, W. H.; Narayanan, S.; Kryatova, O. P.; Richert, C. Org. Lett. 2003, 5, 247-250.
32. Uhlmann, E.; Engels, J. Tetrahedron Lett. 1986, 27, 1023-1026.
33. Connors, W. H.; Narayanan, S.; Kryatova, O. P.; Riehert, C. Org. Lett. 2003, 5, 247-250.
34. Naimi, E.; Zhou A.; Khalili, P.; Wiebe, L. I.; Balzarini, J.; De Clercq, E.; Knaus E. J. Med. Chem. 2003, 46, 995-1004.
35. Czernecki, S.; Valéry, J.-M. Synthesis 1991, 239-240.
36. Asakura, J.; Robins, J. R. J. Org. Chem. 1990, 55, 4928-4933.
37. Lyssenko, K., A.; Lenev, D. A.; Kostyanovsky, R. G. Tetrahedron 2002, 58, 8525-8537.
38. Brotzel, F. Diploma Thesis, University of Konstanz, Konstanz, Germany, 2002; see also Supporting Information.
39. Khan, S. I.; Grinstaff: M. W. J. Am. Chem. Soc. 1999, 121, 4704-4705.
40. (a) Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202-204.
41. (b) Vassiliki, T.; Valentine, R.; Alexandras, S.; Evangelos, Z.; Argyro, E.; Dimitriou, M. Tetrahedron Lett. 2005, 46, 1357-1360.
42. Kottysch, T.; Ahlborn, C.; Brotzel, F.; Richert, C. Chem. Eur. J. 2004, 10, 4017-4028.
43. Schwope, I.; Bleczinski, C. F.; Richert, C. J. Org. Chem. 1999, 64, 4749-4761.
44. Bleczinski, C. F.; Richert, C. J. Am. Chem. Soc. 1999, 121, 10889-10894.
45. (b) Tuma, J.; Richert, C. Biochemistry 2003, 42, 8957-8965.
46. Narayanan, S.; Gall, J.; Richert, C. Nucleic Acids Res. 2004, 32, 2901-2911.
47. Dogan, Z.; Paulini, R.; Rojas Stütz, J. A.; Narayanan, S.; Richert, C. J. Am. Chem. Soc. 2004, 126, 4762-4763.
48. (b) Tuma, J.; Paulini, R.; Rojas Stütz, J. A.; Richert, C. Biochemistry 2004, 43, 15680-15687.
49. Kryatova, O. P.; Connors, W. H.; Bleczinski, C. F.; Mokhir, A. A.; Richert, C. Org. Lett. 2001, 3, 987-990.
50. (b) Siegmund, K.; Maheshwary, S.; Narayanan, S.; Connors, W.; Riedrich, M.; Printz, M.; Richert, C. Nucleic Acids Res. 2005, 33, 4838-4848.
51. Newton-Cheh, C.; Hirschhorn, J. N. Mutat. Res. 2005, 573, 54-69.
52. (b) Gewin, V. Nature 2005, 435, 1159.
53. (c) Craig, D. W.; Stephan, D. A. Expert Rev. Mol. Diagn. 2005, 5, 159-170.
54. Shendure, J.; Porreca, G. J.; Reppas, N. B.; Lin, X.; McCutheon, J. P.; Rosenbaum, A. M.; Wang, M. D.; Zhang, K.; Mitra, R. D.; Church, G. M. Science 2005, 309, 1728-1732.
55. Spies, S.; Griesang, N.; Richert, C. University of Karlsruhe, Karlsruhe, Germany, 2005. Unpublished results.
56. Plutowski, U.; Richert, C. Angew. Chem. 2005, 117, 627-631;
57. Angew. Chem., Int. Ed. 2005, 44, 621-625.
58. Doublie, S.; Tabor, S.; Long, A. M.; Richardson, C. C.; Ellenberger, T. Nature 1998, 391, 251-258.
59. Altman, R. K.; Schwope, I.; Sarracino, D. A.; Tetzlaff, C. N.; Bleczinski, C. F.; Richert, C. J. Comb. Chem. 1999, 1, 493-508.
60. (b) Berlin, K.; Jain, R. K.; Tetzlaff, C.; Steinbeck, C.; Richert, C. Chem. Biol. 1997, 4, 63-77.
61. Dombi, K. L.; Steiner, U. E.; Richert, C. J. Comb. Chem. 2003, 5, 45-60.
62. Gryaznov, S. M. Biochim. Biophys. Acta 1999, 1489, 131-140.
63. Barnes, T. W.; Turner, D. H. J. Am. Chem. Soc. 2001, 123, 4107-4118.
64. Nguyen, H. K.; Fournier, O.; Asseline, U.; Dupret, D.; Thuong, N. T. Nucleic Acids Res. 1999, 27, 1492-1498.
65. Amedio, J. C.; Sunay, U. B.; Repic, O. Synth. Comm. 1995, 25, 667-680
66. Sarracino, D.; Richert, C. Bioorg. Med. Chem. Lett. 1996, 6, 2543-2548.