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Making carbon-nitrogen bonds in biological and chemical synthesis

The function of many biologically active molecules requires the presence of carbon-nitrogen bonds in strategic positions. The biosynthetic pathways leading to such bonds can be bypassed through chemical synthesis to synthesize natural products more efficiently and also to generate the molecular diversity unavailable in nature.

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Figure 1: Nitrogen-containing fragments are key to biological activity.
Figure 2
Figure 3: Oxygen transfer: monooxygenase versus synthetic catalysts.

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  1. Paterson, I. & Anderson, E.A. Science 310, 451–453 (2005).

    Article  Google Scholar 

  2. Newman, D.J., Cragg, G.M. & Snader, K.M. J. Nat. Prod. 66, 1022–1037 (2003).

    Article  CAS  Google Scholar 

  3. Kingston, D.G.I. & Newman, D.J. Curr. Opin. Drug. Disc. Dev. 5, 304–316 (2002).

    Google Scholar 

  4. Burke, M.D., Berger, E.M. & Schreiber, S.L. Science 302, 613–618 (2003).

    Article  CAS  Google Scholar 

  5. Henkel, T., Brunne, R.M., Muller, H. & Reichel, F. Angew. Chem. Int. Edn. Engl. 38, 643–647 (1999).

    Article  CAS  Google Scholar 

  6. Fuerst, S., Hosztafi, S. & Friedmann, T. Curr. Med. Chem. 1, 423–440 (1995).

    CAS  Google Scholar 

  7. Zheng, S. et al. J. Chem. Inf. Model. 45, 856–862 (2005).

    Article  CAS  Google Scholar 

  8. Sharpless, K.B. Angew. Chem. Int. Edn. Engl. 41, 2024–2032 (2002).

    Article  CAS  Google Scholar 

  9. Breslow, R., Nemo, T.E. & Myers, R.S. J. Am. Chem. Soc. 101, 1032–1033 (1979).

    Article  Google Scholar 

  10. Jacobsen, E.N., Zhang, W., Muci, A.R., Ecker, J.R. & Deng, L. J. Am. Chem. Soc. 113, 7063–7064 (1991).

    Article  CAS  Google Scholar 

  11. Grue-Sorensen, G. & Spenser, I.D. J. Am. Chem. Soc. 105, 7401–7404 (1983).

    Article  CAS  Google Scholar 

  12. Hinman, A. & Du Bois, J. J. Am. Chem. Soc. 125, 11510–11511 (2003).

    Article  CAS  Google Scholar 

  13. Nicolaou, K.C. et al. J. Am. Chem. Soc. 122, 9968–9976 (2000).

    Article  CAS  Google Scholar 

  14. Walsh, C.T. Science 303, 1805–1810 (2004).

    Article  CAS  Google Scholar 

  15. Merkx, M. et al. Angew. Chem. Int. Edn. Engl. 40, 2782–2807 (2001).

    Article  CAS  Google Scholar 

  16. Reetz, M.T., Bocola, M., Carballeira, J.D., Zha, D. & Vogel, A. Angew. Chem. Int. Edn. Engl. 44, 4192–4196 (2005).

    Article  CAS  Google Scholar 

  17. Williams, P.A. et al. Science 305, 683–686 (2004).

    Article  CAS  Google Scholar 

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Hili, R., Yudin, A. Making carbon-nitrogen bonds in biological and chemical synthesis. Nat Chem Biol 2, 284–287 (2006). https://doi.org/10.1038/nchembio0606-284

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