Display options
Share it on

Synlett. 2017 Jul;28(12):2407-2421. doi: 10.1055/s-0036-1588778. Epub 2017 Mar 10.

Substituent Effects on Carbon Acidity in Aqueous Solution and at Enzyme Active Sites.

Synlett : accounts and rapid communications in synthetic organic chemistry

Tina L Amyes, John P Richard

Affiliations

  1. Department of Chemistry, University at Buffalo, SUNY, Buffalo, NY 14260-3000.

PMID: 28993718 PMCID: PMC5630183 DOI: 10.1055/s-0036-1588778

Abstract

Methods are described for the determination of p

Keywords: Carbon Acids; Catalysis; Enolates; Enzyme; Imidazole Carbenes; Proton Transfer; Pyridoxal

References

  1. Chem Rev. 2000 Jan 12;100(1):39-92 - PubMed
  2. Bioorg Chem. 2004 Oct;32(5):354-66 - PubMed
  3. Proc Natl Acad Sci U S A. 2006 Jun 6;103(23):8668-73 - PubMed
  4. J Am Chem Soc. 2011 May 4;133(17):6545-8 - PubMed
  5. J Am Chem Soc. 2008 Feb 6;130(5):1574-5 - PubMed
  6. Biochemistry. 1988 Jul 12;27(14 ):5044-53 - PubMed
  7. Org Biomol Chem. 2005 Jun 7;3(11):2145-9 - PubMed
  8. J Am Chem Soc. 1998 Apr 15;120(14):3474-84 - PubMed
  9. Biochemistry. 2005 Feb 22;44(7):2610-21 - PubMed
  10. Biochim Biophys Acta. 2011 Nov;1814(11):1419-25 - PubMed
  11. J Am Chem Soc. 2004 Apr 7;126(13):4167-80 - PubMed
  12. Biochemistry. 1992 Sep 1;31(34):7899-907 - PubMed
  13. Org Lett. 2002 Oct 17;4(21):3587-90 - PubMed
  14. Biochemistry. 1975 Oct 7;14(20):4515-22 - PubMed
  15. Proc Natl Acad Sci U S A. 2006 Feb 7;103(6):1705-10 - PubMed
  16. J Am Chem Soc. 2004 Sep 1;126(34):10538-9 - PubMed
  17. J Am Chem Soc. 2009 Jun 24;131(24):8513-21 - PubMed
  18. J Am Chem Soc. 2002 Mar 27;124(12):2957-68 - PubMed
  19. J Am Chem Soc. 2012 Dec 19;134(50):20421-32 - PubMed
  20. Acc Chem Res. 2001 Dec;34(12):981-8 - PubMed
  21. Org Lett. 2006 Aug 17;8(17):3785-8 - PubMed
  22. Acc Chem Res. 2005 May;38(5):379-85 - PubMed
  23. J Am Chem Soc. 2001 Aug 15;123(32):7949-50 - PubMed
  24. J Am Chem Soc. 2010 Apr 21;132(15):5515-21 - PubMed
  25. Biochemistry. 2013 Oct 22;52(42):7500-11 - PubMed
  26. J Am Chem Soc. 2009 Nov 4;131(43):15815-24 - PubMed
  27. J Phys Chem B. 2007 Nov 1;111(43):12573-81 - PubMed
  28. J Am Chem Soc. 2002 Jul 17;124(28):8251-9 - PubMed
  29. Curr Opin Chem Biol. 2009 Oct;13(4):475-83 - PubMed
  30. Biochemistry. 2004 Aug 3;43(30):9685-94 - PubMed
  31. J Org Chem. 2011 Aug 5;76(15):5907-14 - PubMed
  32. J Org Chem. 2006 Sep 1;71(18):7094-6 - PubMed
  33. J Phys Chem A. 2006 Jan 19;110(2):717-25 - PubMed
  34. J Am Chem Soc. 2011 Mar 9;133(9):3173-83 - PubMed
  35. Biochemistry. 2005 Feb 22;44(7):2622-31 - PubMed
  36. Nature. 2007 Jun 14;447(7146):817-22 - PubMed
  37. Curr Opin Chem Biol. 2014 Aug;21:1-10 - PubMed
  38. Nature. 1976 Jul 22;262(5566):279-81 - PubMed
  39. Nat Struct Biol. 1999 May;6(5):422-6 - PubMed
  40. Bioorg Chem. 2008 Dec;36(6):295-8 - PubMed
  41. J Am Chem Soc. 2013 Nov 13;135(45):16968-76 - PubMed
  42. J Am Chem Soc. 2008 Feb 13;130(6):2041-50 - PubMed
  43. J Am Chem Soc. 2012 Sep 5;134(35):14580-94 - PubMed
  44. Biochemistry. 2003 Jul 15;42(27):8354-61 - PubMed
  45. Nature. 1948 May 8;161(4097):707-9 - PubMed
  46. J Am Chem Soc. 2007 Mar 14;129(10):3013-21 - PubMed
  47. Science. 1995 Jan 6;267(5194):90-3 - PubMed
  48. J Am Chem Soc. 2004 Apr 7;126(13):4366-74 - PubMed

Publication Types

Grant support