Protein Modification by Strain‐Promoted Alkyne–Nitrone Cycloaddition

Abstract

Quicker and slicker: An efficient metal-free 1,3-dipolar cycloaddition of dibenzocyclooctynes with nitrones proceeded with rate constants of up to 39 M−1 s−1, or up to 300 times faster than similar reactions with azides. This strategy is useful for the site-specific N-terminal modification of peptides and proteins (see scheme).

Shown for reading. Its publisher allows quoting it, not republishing it.

References 45

1. 1.

   Prescher JA, Bertozzi CR. Nat. Chem. Biol. 2005;1:13-21.

   Not in our library10.1038/nchembio0605-13

2. 2.

   Sletten EM, Bertozzi CR. Angew. Chem. 2009;121:7108-7133.

   Not in our library10.1002/anie.200900942

3. 3.

   Saxon E, Bertozzi CR. Science. 2000;287:2007-2010.

   Not in our library10.1126/science.287.5460.2007

4. 4.

   Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002;41:2596-2599.

   Not in our library

5. 5.

   Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. 2002;114:2708-2711.

   Not in our library10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4

6. 6.

   Blomquist AT, Liu LH. J. Am. Chem. Soc. 1953;75:2153-2154.

   Not in our library

7. 7.

   Agard NJ, Prescher JA, Bertozzi CR. J. Am. Chem. Soc. 2004;126:15046-15047.

   Not in our library10.1021/ja044996f

8. 8.

   Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Miller IA, Lo A, Codelli JA, Bertozzi CR. Proc. Natl. Acad. Sci. USA. 2007;104:16793-16797.

   Not in our library10.1073/pnas.0707090104

9. 9.

   Lutz JF. Angew. Chem. 2008;120:2212-2214.

   Not in our library

10. 10.

    Becer CR, Hoogenboom R, Schubert US. Angew. Chem. 2009;121:4998-5006.

    Not in our library10.1002/anie.200900755

11. 11.

    Kalia J, Raines TR. Curr. Org. Chem. 2010;14:138-147.

    Not in our library10.2174/138527210790069839

12. 12.

    Agard NJ, Baskin JM, Prescher JA, Lo A, Bertozzi CR. ACS Chem. Biol. 2006;1:644-648.

    Not in our library10.1021/cb6003228

13. 13.

    Link AJ, Vink MKS, Agard NJ, Prescher JA, Bertozzi CR, Tirrell DA. Proc. Natl. Acad. Sci. USA. 2006;103:10180-10185.

    Not in our library10.1073/pnas.0601167103

14. 14.

    Tanrikulu IC, Schmitt E, Mechulam Y, Goddard WA, Tirrell DA. Proc. Natl. Acad. Sci. USA. 2009;106:15285-15290.

    Not in our library10.1073/pnas.0905735106

15. 15.

    Lallana E, Fernandez-Megia E, Riguera R. J. Am. Chem. Soc. 2009;131:5748-5750.

    Not in our library10.1021/ja8100243

16. 16.

    Kele P, Mezö G, Achats F, Wolfbeis OS. Angew. Chem. 2009;121:350-353.

    Not in our library10.1002/anie.200804514

17. 17.

    Fernández-Suárez M, Baruah H, Martínez-Hernández L, Xie KT, Baskin JM, Bertozzi CR, Ting AY. Nat. Biotechnol. 2007;25:1483-1487.

    Not in our library10.1038/nbt1355

18. 18.

    Neef AB, Schultz C. Angew. Chem. 2009;121:1526-1529.

    Not in our library10.1002/anie.200805507

19. 19.

    Nessen MA, Kramer G, Back JW, Baskin JM, Smeenk LEJ, de Koning LJ, van Maarseveen JH, de Jong L, Bertozzi CR, Hiemstra H, de Koster CG. J. Proteome Res. 2009;8:3702-3711.

    Not in our library10.1021/pr900257z

20. 20.

    Wilson JT, Krishnamurthy VR, Cui W, Qu Z, Chaikof EL. J. Am. Chem. Soc. 2009;131:18228-18229.

    Not in our library10.1021/ja908887v

21. 21.

    Ning X, Guo J, Wolfert MA, Boons G.-J. Angew. Chem. 2008;120:2285-2287.

    Not in our library10.1002/anie.200705456

22. 22.

    Debets MF, van Berkel SS, Schoffelen S, Rutjes FPJT, van Hest JCM, van Delft FL. Chem. Commun. 2010;46:97-99.

    Not in our library10.1039/b917797c

23. 23.

    This reference’s wording can’t be shown under the paper’s licence.

    Not in our library

24. 24.

    Huisgen R, Seidl H, Bruning I. Chem. Ber. 1969;102:1102.

    Not in our library

25. 25.

    Dolbier WR, Wicks GE, Burkholder CR. J. Org. Chem. 1987;52:2196-2201.

    Not in our library

26. 26.

    This reference’s wording can’t be shown under the paper’s licence.

    Not in our library

27. 27.

    Gholami MR, Yangjeh AH. J. Chem. Res. Synop. 1999;3:226-227.

    Not in our library

28. 28.

    Butler RN, Coyne AG, Cunningham WJ, Burke LA. J. Chem. Soc. Perkin Trans. 2. 2002;1807-1815.

    Not in our library

29. 29.

    Poloukhtine AA, Mbua NE, Wolfert MA, Boons GJ, Popik VV. J. Am. Chem. Soc. 2009;131:15769-15776.

    Not in our library10.1021/ja9054096

30. 30.

    Merino P, Padwa A. Science of Synthesis, Vol. 27. 2004;511-580.

    Not in our library

31. 31.

    Geoghegan KF, Stroh JG. Bioconjugate Chem. 1992;3:138-146.

    Not in our library10.1021/bc00014a008

32. 32.

    Emery T, Neilands JB. J. Am. Chem. Soc. 1960;82:4903-4904.

    Not in our library

33. 33.

    Dirksen A, Hackeng TM, Dawson PE. Angew. Chem. 2006;118:7743-7746.

    Not in our library10.1002/anie.200602877

34. 34.

    Baggiolini M, Clark-Lewis I. FEBS Lett. 1991;307:97-101.

    Not in our library10.1016/0014-5793(92)80909-z

35. 35.

    van der Laken CJ, Boerman OC, Oyen WJG, van de Ven MTP, van der Meer JWM, Corstens FHM. J. Nucl. Med. 2000;41:463-469.

    Not in our library

36. 36.

    Carrico IS. Chem. Soc. Rev. 2008;37:1423-1431.

    Not in our library10.1039/b703364h

37. 37.

    Hackenberger CPR, Schwarzer D. Angew. Chem. 2008;120:10182-10228.

    Not in our library

38. 38.

    Dondoni A, Massi A, Nanni P, Roda A. Chem. Eur. J. 2009;15:11444-11449.

    Not in our library10.1002/chem.200901746

39. 39.

    McKay CS, Moran J, Pezacki JP. Chem. Commun. 2010;46:931-933.

    Not in our library10.1039/b921630h

40. 40.

    Gilmore JM, Scheck RA, Esser-Kahn AP, Joshi NS, Francis MB. Angew. Chem. 2006;118:5433-5437.

    Not in our library10.1002/anie.200600368

Cited by papers we hold 1

• Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides · 2016
  No notice

Reads

A person counts once a day per paper. We keep no cookie and no address: a reader is a hash that changes every day. Any month under five reads shows no number.