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Organic chemistry

Amide bonds made in reverse

Amide bonds connect the amino acids in proteins and occur in many other useful molecules. An amide-forming reaction that turns the conventional approach on its head offers a practical way of making these bonds.

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Figure 1: Polarity reversal in amide synthesis.

References

  1. Shen, B., Makley, D. M. & Johnston, J. N. Nature 465, 1027–1032 (2010).

    Article  ADS  CAS  Google Scholar 

  2. Williamson, J. R. Cell 139, 1041–1043 (2009).

    Article  CAS  Google Scholar 

  3. Yonath, A. Angew. Chem. Int. Edn 49, 4340–4354 (2010).

    Article  CAS  Google Scholar 

  4. Montalbetti, C. A. G. N. & Falque, V. Tetrahedron 61, 10827–10852 (2005).

    Article  CAS  Google Scholar 

  5. Sheehan, J. C. & Hess, G. P. J. Am. Chem. Soc. 77, 1067–1068 (1955).

    Article  CAS  Google Scholar 

  6. Merrifield, R. B. Angew. Chem. Int. Edn Engl. 24, 799–810 (1985).

    Article  Google Scholar 

  7. Köhn, M. & Breinbauer, R. Angew. Chem. Int. Edn 43, 3106–3116 (2004).

    Article  Google Scholar 

  8. Kent, S. B. H. Chem. Soc. Rev. 38, 338–351 (2009).

    Article  CAS  Google Scholar 

  9. Gunanathan, C., Ben-David, Y. & Milstein, D. Science 317, 790–792 (2007).

    Article  ADS  CAS  Google Scholar 

  10. Valeur, E. & Bradley, M. Chem. Soc. Rev. 38, 606–631 (2009).

    Article  CAS  Google Scholar 

  11. Seebach, D. Angew. Chem. Int. Edn Engl. 18, 239–258 (1979).

    Article  Google Scholar 

  12. Singh, A., Yoder, R. A., Shen, B. & Johnston, J. N. J. Am. Chem. Soc. 129, 3466–3467 (2007).

    Article  CAS  Google Scholar 

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Scheidt, K. Amide bonds made in reverse. Nature 465, 1020–1022 (2010). https://doi.org/10.1038/4651020a

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