Robust Suzuki-Miyaura cross-coupling on DNA-linked substrates

ACS Combinatorial Science

Volumn 17, Issue 1, 2015, Pages 1-4

  Ding, Yun ^a   Clark, Matthew A ^a,b  

^a GLAXOSMITHKLINE   (United States)

^b X Chem Incorporated   (United States)

Author keywords

DNA encoded library technology; Suzuki Miyaura cross coupling

Indexed keywords

DNA;

CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY;

CATALYSIS; DNA; SUBSTRATE SPECIFICITY;

EID: 84921030628     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co5001037     Document Type: Article

References (29)

1. Brenner, S.; Lerner, R. A. Encoded combinatorial chemistry Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5381-5383
2. Kleiner, R. E.; Dumelin, C. E.; Liu, D. R. Small-molecule discovery from DNA-encoded chemical libraries Chem. Soc. Rev. 2011, 40, 5701-5717
3. Mannocci, L.; Leimbacher, M.; Wichert, M.; Scheuermann, J.; Neri, D. 20 years of DNA-encoded chemical libraries Chem. Commun. 2011, 47, 12747-12753
4. Clark, M. A. Selecting Chemicals: The emerging utility of DNA-encoded librareis Curr. Opin. Chem. Biol. 2010, 14, 396-403
5. Clark, M. A.; Acharya, R. A.; Arico-Muendel, C. C.; Belyanskaya, S. L.; Benjamin, D. R.; Carlson, N. R.; Centrella, P. A.; Chiu, C. H.; Creaser, S. P.; Cuozzo, J. W.; Davie, C. P.; Ding, Y.; Franklin, G. J.; Franzen, K. D.; Gefter, M. L.; Hale, S. P.; Hansen, N. J. V.; Israel, D. I.; Jiang, J.; Kavarana, M. J.; Kelley, M. S.; Kollmann, C. S.; Li, F.; Lind, K.; Mataruse, S.; Medeiros, P. F.; Messer, J. A.; Myers, P.; OKeefe, H.; Oliff, M. C.; Rise, C. E.; Satz, A. L.; Skinner, S. R.; Svendsen, J. L.; Tang, L.; Vloten, K. V.; Wagner, R. W.; Yao, G.; Zhao, B.; Morgan, B. A. Design, synthesis and selection of DNA-encoded small-molecule libraries Nat. Chem. Biol. 2009, 5, 647-654
6. Deng, H.; OKeefe, H.; Davie, C. P.; Lind, K. E.; Acharya, R. A.; Franklin, G. J.; Larkin, J.; Matico, R.; Neeb, M.; Thompson, M. M.; Lohr, T.; Gross, J. W.; Centrella, P. A.; ODonovan, G. K.; Bedard, K. L.; Vloten, K.-v.; Mataruse, S.; Skinner, S. R.; Belyanskaya, S. L.; Carpenter, T. Y.; Shearer, T. W.; Clark, M. A.; Cuozzo, J. W.; Arico-Muendel, C. C.; Morgan, B. A. Discovery of Highly Potent and Selective Small Molecule ADAMTS-5 Inhibitors That Inhibit Human Cartilage Degradation via Encoded Library Technology (ELT) J. Med. Chem. 2012, 55, 7061-7079
7. Gentile, G.; Merlo, G.; Pozzan, A.; Bernasconi, G.; Bax, B.; Bamborough, P.; Bridges, A.; Carter, P.; Neu, M.; Yao, G.; Brough, C.; Cutler, G.; Coffin, A.; Belyanskaya, S. 5-Aryl-4-carboxamide-1,3-oxazoles: Potent and Selective GSK-3 Inhibitors Bioorg. Med. Chem. Lett. 2012, 22, 1989-1994
8. Disch, J. S.; Evindar, G.; Chiu, C. H.; Blum, C. A.; Dai, H.; Jin, L.; Schuman, E.; Lind, K. E.; Belyanskaya, S. L.; Deng, J.; Coppo, F.; Aquilani, L.; Graybill, T. L.; Cuozzo, J. W.; Lavu, S.; Mao, C.; Vlasuk, G. P.; Perni, R. B. Discovery of Thieno[3,2- d ]pyrimidine-6-carboxamides as Potent Inhibitors of SIRT1, SIRT2, and SIRT3 J. Med. Chem. 2013, 56, 3666-3679
9. Ding, Y. Preparation of 2,4-Diamino 1,3,5-Triazine and 4,6-Diaminopyrimidine Derivatives as Aggrecanase Inhibitors. PCT Int. Appl. WO2010085246 A1 20100729, 2010.
10. Halpin, D. R.; Lee, J. A.; Wrenn, S. J.; Harbury, P. B. DNA Display III. Solid-Phase Organic Synthesis on Unprotected DNA PLoS Biol. 2004, 2 (7) 1031
11. Wrenn, S. J.; Weisinger, R. M.; Halpin, D. R.; Harbury, P. B. Synthetic Ligands Discovered by in Vitro Selection J. Am. Chem. Soc. 2007, 129 (43) 13137
12. Li, X.; Liu, D. R. DNA-Templated Organic Synthesis: Natures Strategy for Controlling Chemical Reactivity Applied to Synthetic Molecules Angew. Chem., Int. Ed. 2004, 43, 4848
13. Gartner, Z. J.; Kanan, M. W.; Liu, D. R. Expanding the Reaction Scope of DNA-Templated Synthesis Angew. Chem., Int. Ed. 2002, 41 (10) 1796
14. Omumi, A.; Beach, D. G.; Baker, M.; Gabryelski, W.; Manderville, R. A. Postsynthetic Guanine Arylation of DNA by Suzuki-Miyaura Cross-Coupling J. Am. Chem. Soc. 2011, 133, 42-50
15. Lercher, L.; McGouran, J. F.; Kessler, B. M.; Schofield, C. J.; Davis, B. G. DNA Modification under Mild Conditions by Suzuki-Miyaura Cross-Coupling for the Generation of Functional Probes Angew. Chem., Int. Ed. 2013, 52, 10553-10558
16. de Meijere, A.; Diederich, F., Eds. Metal-Catalyzed Cross-coupling Reactions, Vol. 2; Wiley-VCH: Weinheim, Germany, 2004.
17. Miyaura, N. Cross-Coupling Reactions Top. Curr. Chem. 2002, 219, 11
18. Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Glivec (STI571, Imatinib), A Rationally Developed, Targeted Anticancer Drug Nat. Rev. Drug Discovery 2002, 1, 493
19. Markham, A.; Goa, K. L. Valsartan Drugs 1997, 54, 299
20. Casalnuovo, A. L.; Calabrese, J. C. Palladium-Catalyzed Alkylations in Aqueous Media J. Am. Chem. Soc. 1990, 112, 4324-4330
21. Genêt, J. P.; Blart, E.; Savignac, M. Palladium-Catalyzed Cross-Coupling Reactions in a Homogeneous Aqueous Medium Synlett 1992, 715-717
22. Genêt, J. P.; Linquist, A.; Blart, E.; Mouries, V.; Savignac, M. Suzuki-Type Cross Coupling Reactions Using Palladium-Water Soluble Catalyst. Synthesis of Functionalized Dienes Tetrahedron Lett. 1995, 36, 1443-1446
23. DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. Aqueous-Phase, Palladium-Catalyzed Cross-Coupling of Aryl Bromides under Mild Conditins, Using Water-Soluble, Sterically Demanding Alkylphosphines J. Org. Chem. 2004, 69, 7919-7927
24. Beller, M.; Krauter, J. G. E.; Zapf, A. Carbohydrate-Substituted Triarylphosphanes-A New Class of Ligands for Two-Phase Catalysis Angew. Chem., Int. Ed. Engl. 1997, 36 (7) 772-774
25. Kudo, N.; Perseghini, M.; Fu, G. C. A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles Angew. Chem., Int. Ed. 2006, 45, 1282
26. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. A Highly Active Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Heteroaryl Compounds Angew. Chem., Int. Ed. 2006, 45, 3484
27. Guram, A. S.; King, A. O.; Allen, J. G.; Wang, X.; Schenkel, L. B.; Chan, J.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J.; Reider, P. J. New Air-Stable Catalysts for General and Efficient Suzuki-Miyaura Cross-Coupling Reactions of Heteroaryl Chlorides Org. Lett. 2006, 8, 1787-1789
28. Itoh, T.; Mase, T. Tetrahedron Lett. 2005, 46, 3573
29. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7141