A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system

Nature Chemistry

Volumn 3, Issue 2, 2011, Pages 146-153

  Chen, Yiyun ^a   Kamlet, Adam S ^a   Steinman, Jonathan B ^a   Liu, David R ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CARBOXYLIC ACID; DNA; RUTHENIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DNA MICROARRAY; LIGHT; OXIDATION REDUCTION REACTION;

AZIDES; CARBOXYLIC ACIDS; DNA; LIGHT; MOLECULAR STRUCTURE; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; OXIDATION-REDUCTION; RUTHENIUM;

EID: 79251640637     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.932     Document Type: Article

References (46)

1. Kanan, M. W., Rozenman, M. M., Sakurai, K., Snyder, T. M. & Liu, D. R. Reaction discovery enabled by DNA-templated synthesis and in vitro selection. Nature 431, 545-549 (2004).
2. Beeler, A. B., Su, S., Singleton, C. A. & Porco, J. A. Discovery of chemical reactions through multidimensional screening. J. Am. Chem. Soc. 129, 1413-1419 (2007).
3. Rozenman, M. M., Kanan, M. W. & Liu, D. R. Development and initial application of a hybridization-independent, DNA-encoded reaction discovery system compatible with organic solvents. J. Am. Chem. Soc. 129, 14933-14938 (2007).
4. Scriven, E. F. V. & Turnbull, K. Azides - their preparation and synthetic uses. Chem. Rev. 88, 297-368 (1988).
5. Johnstone, R. A. W., Wilby, A. H. & Entwistle, I. D. Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds. Chem. Rev. 85, 129-170 (1985).
6. Bayley, H., Standring, D. N. & Knowles, J. R. Propane-1,3-dithiol - selective reagent for efficient reduction of alkyl and aryl azides to amines. Tetrahedron Lett. 19, 3633-3634 (1978).
7. Gololobov, Y. G. & Kasukhin, L. F. Recent advances in the Staudinger reaction. Tetrahedron 48, 1353-1406 (1992).
8. Burns, J. A., Butler, J. C., Moran, J. & Whitesides, G. M. Selective reduction of disulfides by tris(2-carboxyethyl)phosphine. J. Org. Chem. 56, 2648-2650 (1991).
9. Maryanoff, B. E. & Reitz, A. B. TheWittig olefination reaction and modifications involving phosphoryl-stabilized carbanions - stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 89, 863-927 (1989).
10. Sakurai, K., Snyder, T. M. & Liu, D. R. DNA-templated functional group transformations enable sequence-programmed synthesis using small-molecule reagents. J. Am. Chem. Soc. 127, 1660-1661 (2005).
11. Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A. & Bertozzi, C. R. A comparative study of bioorthogonal reactions with azides. ACS Chem. Biol. 1, 644-648 (2006).
12. Brase, S., Gil, C., Knepper, K. & Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 44, 5188-5240 (2005).
13. Kohn, M. & Breinbauer, R. The Staudinger ligation - a gift to chemical biology. Angew. Chem. Int. Ed. 43, 3106-3116 (2004).
14. Kolb, H. C. & Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discov. Today 8, 1128-1137 (2003).
15. Valeur, E. & Bradley, M. Amide bond formation: beyond the myth of coupling reagents. Chem. Soc. Rev. 38, 606-631 (2009).
16. Sletten, E. M. & Bertozzi, C. R. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48, 6974-6998 (2009).
17. Hermanson, G. T. Bioconjugate Techniques. 2nd edn, 169-181 (Academic, 2008).
18. Basle, E., Joubert, N. & Pucheault, M. Protein chemical modification on endogenous amino acids. Chem. Biol. 17, 213-227 (2010).
19. Meldal, M. & Tornoe, C. W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 108, 2952-3015 (2008).
20. Holmberg, A. et al. The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis 26, 501-510 (2005).
21. Solabannavar, S. B., Helavi, V. B., Desai, U. V. & Mane, R. B. A novel short synthesis of norbisabolide. Tetrahedron Lett. 43, 4535-4536 (2002).
22. Baciocchi, E., Dellaira, D. & Ruzziconi, R. Dimethyl arylmalonates from cerium(IV) ammonium-nitrate promoted reactions of dimethyl malonate with aromatic compounds in methanol. Tetrahedron Lett. 27, 2763-2766 (1986).
23. Poulsen, T. B. & Jorgensen, K. A. Catalytic asymmetric Friedel-Crafts alkylation reactions - copper showed the way. Chem. Rev. 108, 2903-2915 (2008).
24. Bandini, M., Melloni, A. & Umani-Ronchi, A. New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction. Angew. Chem. Int. Ed. 43, 550-556 (2004).
25. Scheiner, P., Schomake, J. H., Deming, S., Libbey,W. J. & Nowack, G. P. Addition of aryl azides to norbornene. A kinetic investigation. J. Am. Chem. Soc. 87, 306-311 (1965).
26. Zhdankin, V. V. & Stang, P. J. Chemistry of polyvalent iodine. Chem. Rev. 108, 5299-5358 (2008).
27. Juris, A. et al. Ru(II) polypyridine complexes: photophysics, photochemistry, electrochemistry, and chemiluminescence. Coord. Chem. Rev. 84, 85-277 (1988).
28. Kalyanasundaram, K. Photophysics, photochemistry and solar-energy conversion with tris(bipyridyl)ruthenium(II) and its analogs. Coord. Chem. Rev. 46, 159-244 (1982).
29. Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes. Science 322, 77-80 (2008).
30. Ischay, M. A., Anzovino, M. E., Du, J. & Yoon, T. P. Efficient visible light photocatalysis of [2+2] enone cycloadditions. J. Am. Chem. Soc. 130, 12886-12887 (2008).
31. Narayanam, J. M. R., Tucker, J. W. & Stephenson, C. R. J. Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenatioin reaction. J. Am. Chem. Soc. 131, 8756-8757 (2009).
32. Yoon, T. P., Ischay, M. A. & Du, J. N. Visible light photocatalysis as a greener approach to photochemical synthesis. Nature Chem. 2, 527-532 (2010).
33. Delaive, P. J., Sullivan, B. P., Meyer, T. J. & Whitten, D. G. Applications of lightinduced electron-transfer reactions - coupling of hydrogen generation with photo-reduction of ruthenium(II) complexes by triethylamine. J. Am. Chem. Soc. 101, 4007-4008 (1979).
34. Su, W., Li, Y. S. & Zhang, Y. M. Samarium diiodide induced reductive coupling of nitriles with azides. J. Chem. Res. (S), 32-33 (2001).
35. Benati, L. et al. Radical reduction of aromatic azides to amines with triethylsilane. J. Org. Chem. 71, 5822-5825 (2006). (Pubitemid 44117042)
36. Hays, D. S. & Fu, G. C. Development of Bu3SnH-catalyzed processes: efficient reduction of azides to amines. J. Org. Chem. 63, 2796-2797 (1998).
37. Borak, J. B. & Falvey, D. E. A new photolabile protecting group for release of carboxylic acids by visible-light-induced direct and mediated electron transfer. J. Org. Chem. 74, 3894-3899 (2009).
38. Fancy, D. A. & Kodadek, T. Chemistry for the analysis of protein-protein interactions: rapid and efficient cross-linking triggered by long wavelength light. Proc. Natl Acad. Sci. USA 96, 6020-6024 (1999).
39. Gill, M. R. et al. A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells. Nature Chem. 1, 662-667 (2009).
40. Raines, R. T. Ribonuclease A. Chem. Rev. 98, 1045-1065 (1998).
41. Lee, H. M., Larson, D. R. & Lawrence, D. S. Illuminating the chemistry of life: design, synthesis, and applications of 'caged' and related photoresponsive compounds. ACS Chem. Biol. 4, 409-427 (2009).
42. Mayer, G. & Heckel, A. Biologically active molecules with a 'light switch'. Angew. Chem. Int. Ed. 45, 4900-4921 (2006).
43. Sinha, R. P. & Hader, D. P. UV-induced DNA damage and repair: a review. Photochem. Photobiol. Sci. 1, 225-236 (2002).
44. Griffin, R. J. et al. The 4-azidoberazyloxycarbonyl function; application as a novel protecting group and potential prodrug modification for amines. J. Chem. Soc. Perkin Trans. 1, 1205-1211 (1996).
45. Wuts, P. G. M. & Greene, T. W. Greene's Protective Groups in Organic Synthesis. 4th edn, 533-646 (Wiley, 2007).
46. Crook, E. M., Mathias, A. P. & Rabin, B. R. Spectrophotometric assay of bovine pancreatic ribonuclease by the use of cytidine 2′-3′- phosphate. Biochem. J. 74, 234-238 (1960).