Display options
Share it on

Chem Sci. 2016 Apr 21;7(4):2657-2665. doi: 10.1039/c5sc03459k. Epub 2016 Jan 11.

Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates.

Chemical science

Laurent Raibaut, Marine Cargoët, Nathalie Ollivier, Yun Min Chang, Hervé Drobecq, Emmanuelle Boll, Rémi Desmet, Jean-Christophe M Monbaliu, Oleg Melnyk

Affiliations

  1. UMR CNRS 8161 CNRS , Université de Lille , Institut Pasteur de Lille , 1 rue du Pr Calmette , 59021 Lille Cedex , France . Email: [email protected].
  2. Center for Integrated Technology and Organic Synthesis , Department of Chemistry , University of Liège , Building B6a, Room 3/16a, Sart-Tilman , B-4000 Liège , Belgium.

PMID: 28660038 PMCID: PMC5477010 DOI: 10.1039/c5sc03459k

Abstract

Given the potential of peptide selenoesters for protein total synthesis and the paucity of methods for the synthesis of these sensitive peptide derivatives, we sought to explore the usefulness of the bis(2-selenylethyl)amido (SeEA) group,

References

  1. Org Lett. 2011 Oct 21;13(20):5588-91 - PubMed
  2. Bioorg Med Chem. 2013 Jun 15;21(12):3473-8 - PubMed
  3. Chembiochem. 2010 Mar 1;11(4):511-5 - PubMed
  4. Org Lett. 2006 Sep 28;8(20):4465-8 - PubMed
  5. Org Lett. 2015 Jul 2;17(13):3354-7 - PubMed
  6. Org Lett. 2001 May 3;3(9):1331-4 - PubMed
  7. Acc Chem Res. 2013 Nov 19;46(11):2475-84 - PubMed
  8. Org Lett. 2013 Jun 7;15(11):2620-3 - PubMed
  9. Org Lett. 2015 Jan 2;17(1):130-3 - PubMed
  10. Methods Enzymol. 2012;503:57-74 - PubMed
  11. Angew Chem Int Ed Engl. 2011 Dec 9;50(50):12042-5 - PubMed
  12. Nature. 2011 Dec 21;480(7378):471-9 - PubMed
  13. J Phys Chem A. 2006 Dec 21;110(50):13394-404 - PubMed
  14. Anal Bioanal Chem. 2007 Oct;389(4):1267-81 - PubMed
  15. Angew Chem Int Ed Engl. 2010 Sep 17;49(39):7049-53 - PubMed
  16. Chem Pharm Bull (Tokyo). 1993 Mar;41(3):502-6 - PubMed
  17. Angew Chem Int Ed Engl. 2011 Jun 27;50(27):6137-41 - PubMed
  18. Org Lett. 2011 Feb 4;13(3):386-9 - PubMed
  19. Org Lett. 2012 Jan 6;14(1):374-7 - PubMed
  20. Bioorg Med Chem. 2013 Jun 15;21(12):3486-94 - PubMed
  21. Org Lett. 2014 Aug 1;16(15):4032-5 - PubMed
  22. Org Lett. 2012 May 4;14(9):2222-5 - PubMed
  23. J Am Chem Soc. 2009 Jul 15;131(27):9475-7 - PubMed
  24. J Am Chem Soc. 2015 Nov 11;137(44):14011-4 - PubMed
  25. Org Lett. 2015 Jul 17;17(14):3636-9 - PubMed
  26. Proc Natl Acad Sci U S A. 2013 Apr 23;110(17):6657-62 - PubMed
  27. Org Lett. 2000 Jun 29;2(13):1939-41 - PubMed
  28. Chem Commun (Camb). 2014 Jan 4;50(1):58-60 - PubMed
  29. Org Lett. 1999 Sep 9;1(5):749-52 - PubMed
  30. Chembiochem. 2011 Aug 16;12(12):1840-4 - PubMed
  31. Nat Chem Biol. 2011 Feb;7(2):113-9 - PubMed
  32. J Am Chem Soc. 2006 May 24;128(20):6640-6 - PubMed
  33. J Am Chem Soc. 1971 Jul 14;93(14):3504-15 - PubMed
  34. J Am Chem Soc. 2006 Jun 7;128(22):7287-90 - PubMed
  35. Angew Chem Int Ed Engl. 2006 Jun 12;45(24):3985-8 - PubMed
  36. Chem Soc Rev. 2013 May 21;42(10):4408-20 - PubMed
  37. Curr Opin Chem Biol. 2014 Oct;22:137-45 - PubMed
  38. Angew Chem Int Ed Engl. 2012 Jan 2;51(1):209-13 - PubMed
  39. Traffic. 2012 Sep;13(9):1261-72 - PubMed
  40. Org Lett. 2009 Feb 19;11(4):823-6 - PubMed
  41. Angew Chem Int Ed Engl. 2010 Nov 22;49(48):9126-31 - PubMed
  42. Science. 1994 Nov 4;266(5186):776-9 - PubMed
  43. Chem Soc Rev. 2009 Feb;38(2):338-51 - PubMed
  44. J Pept Sci. 2014 Feb;20(2):92-7 - PubMed
  45. Angew Chem Int Ed Engl. 2012 Feb 6;51(6):1481-6 - PubMed
  46. Org Lett. 2000 Jul 13;2(14):2141-3 - PubMed
  47. Biopolymers. 2010;94(4):414-22 - PubMed
  48. Angew Chem Int Ed Engl. 2006 Feb 13;45(8):1248-52 - PubMed
  49. Chem Commun (Camb). 2015 Apr 14;51(29):6395-8 - PubMed
  50. J Org Chem. 2011 May 6;76(9):3194-202 - PubMed
  51. Nat Protoc. 2015 Feb;10(2):269-92 - PubMed
  52. Chem Commun (Camb). 2009 Jan 28;(4):407-9 - PubMed
  53. Anal Chem. 2002 Jul 1;74(13):3239-46 - PubMed
  54. Org Lett. 2013 Nov 1;15(21):5516-9 - PubMed
  55. Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1232-40 - PubMed
  56. Org Lett. 2010 Nov 19;12(22):5238-41 - PubMed
  57. Org Lett. 2011 Mar 18;13(6):1560-3 - PubMed
  58. J Am Chem Soc. 2004 Sep 1;126(34):10508-9 - PubMed
  59. Chem Sci. 2015 Mar 1;6(3):2110-2121 - PubMed
  60. Angew Chem Int Ed Engl. 1998 Feb 16;37(3):347-349 - PubMed
  61. Chem Sci. 2016 Jan 1;7(1):339-345 - PubMed

Publication Types