Postsynthetic DNA modification through the copper-catalyzed azide-alkyne cycloaddition reaction

Angewandte Chemie - International Edition

Volumn 47, Issue 44, 2008, Pages 8350-8358

  Gramlich, Philipp M E ^a,b   Wirges, Christian T ^a   Manetto, Antonio ^a,b   Carell, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b Baseclick GmbH   (Germany)

Author keywords

Bioconjugation; Click chemistry; DNA; Polymerase chain reaction; Solid phase synthesis

Indexed keywords

ABS RESINS; ACETYLENE; COPPER; CYCLOADDITION; DNA; GENES; HYDROCARBONS; NITROGEN COMPOUNDS; OLIGONUCLEOTIDES; ORGANIC ACIDS;

BIOCONJUGATION; BIOMEDICAL RESEARCHES; CLICK CHEMISTRY; CYCLOADDITION REACTIONS; DNA MODIFICATIONS; DNA STRANDS; FUNCTIONAL NANOMATERIALS; FUNCTIONALIZATION; FUNCTIONALIZED; GENE FRAGMENTS; HIGH PURITIES; HIGH QUALITIES; HUISGEN CYCLOADDITION; LABELING METHODS; MOLECULAR DIAGNOSTICS; POLYMERASE CHAIN REACTION; POLYNUCLEOTIDES; REACTION YIELDS;

NUCLEIC ACIDS;

ALKYNE; AZIDE; COPPER; DNA; ENZYME; NANOMATERIAL; PROTEIN;

BIOSYNTHESIS; CATALYSIS; CHEMISTRY; SHORT SURVEY; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; DNA; ENZYMES; NANOSTRUCTURES; PROTEINS;

EID: 54249161798     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802077     Document Type: Short Survey

References (71)

1. R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York, 1984, pp. 1-176.
2. J.-F. Lutz, Angew. Chem. 2007, 119, 1036-1043;
3. Angew. Chem. Int. Ed. 2007, 46, 1018-1025;
4. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
5. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064;
6. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711;
7. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
8. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075;
9. Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
10. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137.
11. V. Aucagne, D. A. Leigh, Org. Lett. 2006, 8, 4505-4507;
12. H. T. Ten Brink, J. T. Meijer, R. V. Geel, M. Damen, D. W. P. M. Löwik, J. C. M. van Hest, J. Pept. Sci. 2006, 12, 686-692.
13. A. E. Speers, B. F. Cravett, Chem. Biol. 2004, 11, 535-546.
14. T. Liebert, C. Hänsch, T. Heinze, Macromol. Rapid Commun. 2006, 27, 208-213.
15. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192-3193.
16. J. A. Link, D. A. Tirrell, J. Am. Chem. Soc. 2003, 125, 11164-11165.
17. C. J. Burrows, J. G. Muller, Chem. Rev. 1998, 98, 1109-1151;
18. S. Thyagarajan, N. N. Murthy, A. A. N. Sarjeant, K. D. Karlin, S. E. Rokita, J. Am. Chem. Soc. 2006, 128, 7003-7008.
19. T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853-2855.
20. L. M. Smith, S. Fung, M. W. Hunkapiller, T. J. Hunkapiller, L. E. Hood, Nucleic Acids Res. 1985, 13, 2399-2412.
21. M. Kuwahara, Y. Takahata, A. Shoji, A. N. Ozaki, H. Ozaki, H. Sawai, Bioorg. Med. Chem. Lett. 2003, 13, 3735-3738;
22. A. Roychowdhury, H. Illangkoon, C. L. Hendrickson, S. A. Benner, Org. Lett. 2004, 6, 489-492;
23. M. Mehedi Masud, M. Kuwahara, H. Ozaki, H. Sawai, Bioorg. Med. Chem. 2004, 12, 1111-1120.
24. I. Géci, V. V. Filichev, E. B. Pedersen, Chem. Eur. J. 2007, 13, 6379-6386.
25. D. I. Rozkiewicz, J. Gierlich, G. A. Burley, K. Gutsmiedl, T. Carell, B. J. Ravoo, D. N. Reinhoudt, ChemBioChem 2007, 8, 1997-2002.
26. A. M. Jawalekar, N. Meeuwenoord, J. G. O. Cremers, H. S. Overkleeft, G. A. van der Marel, F. P. J. T. Rutjes, F. L. v. Delft, J. Org. Chem. 2008, 73, 287-290.
27. T. S. Seo, Z. Li, H. Ruparel, J. Ju, J. Org. Chem. 2003, 68, 609-612.
28. Z. Li, T. S. Seo, J. Ju, Tetrahedron Lett. 2004, 45, 3143-3146.
29. T. S. Seo, X. Bai, H. Ruparel, Z. Li, N. J. Turro, J. Ju, Proc. Natl. Acad. Sci. USA 2004, 101, 5488-5493;
30. T. S. Seo, X. Bai, D. H. Kim, Q. Meng, S. Shi, H. Ruparel, Z. Li, N. J. Turro, J. Ju, Proc. Natl. Acad. Sci. USA 2005, 102, 5926-5931.
31. N. K. Devaraj, G. P. Miller, W. Ebina, B. Kakaradov, J. P. Collman, E. T. Kool, C. E. D. Chidsey, J. Am. Chem. Soc. 2005, 127, 8600-8601.
32. S. Mazzini, F. Garcia-Martin, M. Alvira, A. Avino, B. Manning, F. Albericio, R. Eritja, Chem. Biodiversity 2008, 5, 209-218;
33. M. Alvira, R. Eritja, Chem. Biodiversity 2007, 4, 2798-2809;
34. K. Gogoi, M. V. Mane, S. S. Kunte, V. A. Kumar, Nucleic Acids Res. 2007, 35, e139;
35. M. Humenik, Y. Huang, Y. Wang, M. Sprinzl, ChemBioChem 2007, 8, 1103-1106.
36. B. P. Duckworth, Y. Chen, J. W. Wollack, Y. Sham, J. D. Mueller, T. A. Taton, M. D. Distefano, Angew. Chem. 2007, 119, 8975-8978;
37. Angew. Chem. Int. Ed. 2007, 46, 8819-8822.
38. R. P. Goodman, I. A. T. Schaap, C. F. Tardin, C. M. Erben, R. M. Berry, C. F. Schmidt, A. J. Turberfield, Science 2005, 310, 1661-1665.
39. M. Nakane, S. Ichikawa, A. Matsuda, Nucleic Acids Symp. Ser. 2005, 49, 189-190.
40. R. Kumar, A. El-Sagheer, J. Tumpane, P. Lincoln, L. M. Wilhelmson, T. Brown, J. Am. Chem. Soc. 2007, 129, 6859-6864.
41. M. Nakane, S. Ichikawa, A. Matsuda, J. Org. Chem. 2008, 73, 1842-1851.
42. J. Lietard, A. Meyer, J.-J. Vasseur, F. Morvan, J. Org. Chem. 2008, 73, 191-200;
43. A. Meyer, C. Bouillon, S. Vidal, J.-J. Vasseur, F. Morvan, Tetrahedron Lett. 2006, 47, 8867-8871.
44. J. Lietard, A. Meyer, J.-J. Vasseur, F. Morvan, Tetrahedron Lett. 2007, 48, 8795-8798.
45. A. V. Ustinov, V. V. Dubnyakova, V. A. Korshun, Tetrahedron 2008, 64, 1467-1473;
46. A. V. Ustinov, V. A. Korshun, Russ. Chem. Bull. 2006, 55, 1268-1274.
47. C. Bouillon, A. Meyer, S. Vidal, A. Jochum, Y. Chevolot, J.-P. Cloarec, J.-P. Praly, J.-J. Vasseur, F. Morvan, J. Org. Chem. 2006, 71, 4700-4701.
48. F. Morvan, A. Meyer, A. Jochum, C. Sabin, Y. Chevolot, A. Imberty, J.-P. Praly, J.-J. Vasseur, E. Souteyrand, S. Vidal, Bioconjugate Chem. 2007, 18, 1637-1643.
49. Y. Chevolot, C. Bouillon, S. Vidal, F. Morvan, A. Meyer, J.-P. Cloarec, A. Jochum, J.-P. Praly, J.-J. Vasseur, E. Souteyrand, Angew. Chem. 2007, 119, 2450-2454;
50. Angew. Chem. Int. Ed. 2007, 46, 2398-2402.
51. A. Salic, T. J. Mitchison, Proc. Natl. Acad. Sci. USA 2008, 105, 2415-2420.
52. D. M. Hammond, A. Manetto, J. Gierlich, V. A. Azov, P. M. E. Gramlich, G. A. Burley, M. Maul, T. Carell, Angew. Chem. 2007, 119, 4262-4265;
53. Angew. Chem. Int. Ed. 2007, 46, 4184-4187.
54. G. A. Burley, J. Gierlich, M. R. Mofid, S. T. H. Nir, Y. Eichen, T. Carell, J. Am. Chem. Soc. 2006, 128, 1398-1399.
55. J. Gierlich, K. Gutsmiedl, P. M. E. Gramlich, A. Schmidt, G. Burley, T. Carell, Chem. Eur. J. 2007, 13, 9486-9494.
56. F. Seela, V. R. Sirivolu, Helv. Chim. Acta 2007, 90, 535-552;
57. F. Seela, V. R. Sirivolu, Chem. Biodiversity 2006, 3, 509-514;
58. F. Seela, V. R. Sirivolu, P. Chittepu, Bioconjugate Chem. 2008, 19, 211-224;
59. F. Seela, V. R. Sirivolu, Nucleosides Nucleotides Nucleic acids 2007, 26, 597-601;
60. P. Kocalka, N. K. Andersen, F. Jensen, P. Nielsen, ChemBioChem 2007, 8, 2106-2116.
61. J. Gierlich, G. A. Burley, P. M. E. Gramlich, D. M. Hammond, T. Carell, Org. Lett. 2006, 8, 3639-3642.
62. P. M. E. Gramlich, S. Warncke, J. Gierlich, T. Carell, Angew. Chem. 2008, 120, 3491-3493;
63. Angew. Chem. Int. Ed. 2008, 47, 3442-3444.
64. P. M. E. Gramlich, C. T. Wirges, J. Gierlich, T. Carell, Org. Lett. 2008, 10, 249-251.
65. M. Fischler, U. Simon, H. Nir, Y. Eichen, G. A. Burley, J. Gierlich, P. M. E. Gramlich, T. Carell, Small 2007, 3, 1049-1055.
66. M. Fischler, A. Sologubenko, J. Mayer, G. Clever, G. Burley, J. Gierlich, T. Carell, U. Simon, Chem. Commun. 2008, 169-171.
67. R. L. Weller, S. R. Rajski, Org. Lett. 2005, 7, 2141-2144;
68. R. L. Weller, S. R. Rajski, ChemBioChem 2006, 7, 243-245.
69. M. Pignot, C. Siethoff, M. Linscheid, E. Weinhold, Angew. Chem. 1998, 110, 3050-3053;
70. Angew. Chem. Int. Ed. 1998, 37, 2888-2891.
71. G. Pljevaljcic, F. Schmidt, A. J. Scheidig, R. Lurz, E. Weinhold, ChemBioChem 2007, 8, 1516-1519.