Display options
Cite
Richard JP. Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions. Pure Appl Chem. 2011;83(8):1555-1565doi: 10.1351/PAC-CON-11-02-05.
Richard, J. P. (2011). Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions. Pure and applied chemistry. Chimie pure et appliquee, 83(8), 1555-1565. https://doi.org/10.1351/PAC-CON-11-02-05
Richard, John P. "Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions." Pure and applied chemistry. Chimie pure et appliquee vol. 83,8 (2011): 1555-1565. doi: https://doi.org/10.1351/PAC-CON-11-02-05
Richard JP. Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions. Pure Appl Chem. 2011 Jul 08;83(8):1555-1565. doi: 10.1351/PAC-CON-11-02-05. PMID: 23505326; PMCID: PMC3596839.
Copy Download .nbib Format: NLM
Share it on

Pure Appl Chem. 2011 Jul 08;83(8):1555-1565. doi: 10.1351/PAC-CON-11-02-05.

Enzymatic Catalysis of Proton Transfer and Decarboxylation Reactions.

Pure and applied chemistry. Chimie pure et appliquee

John P Richard

Affiliations

  1. Department of Chemistry, University at Buffalo, Buffalo, NY, 14260, USA.

PMID: 23505326 PMCID: PMC3596839 DOI: 10.1351/PAC-CON-11-02-05

Abstract

Deprotonation of carbon and decarboxylation at enzyme active sites proceed through the same carbanion intermediates as for the uncatalyzed reactions in water. The mechanism for the enzymatic reactions can be studied at the same level of detail as for nonenzymatic reactions, using the mechanistic tools developed by physical organic chemists. Triosephosphate isomerase (TIM) catalyzed interconversion of D-glyceraldehyde 3-phosphate and dihydroxyacetone phosphate is being studied as a prototype for enzyme catalyzed proton transfer, and orotidine monophosphate decarboxylase (OMPDC) catalyzed decarboxylation of orotidine 5'-monophosphate is being studied as a prototype for enzyme-catalyzed decarboxylation.

References

  1. J Am Chem Soc. 2007 Aug 29;129(34):10330-1 - PubMed
  2. Biochemistry. 2009 Jun 23;48(24):5518-31 - PubMed
  3. Biochemistry. 2008 Apr 22;47(16):4575-82 - PubMed
  4. J Am Chem Soc. 2008 Feb 6;130(5):1574-5 - PubMed
  5. Biochemistry. 1994 Mar 15;33(10):2815-23 - PubMed
  6. Org Biomol Chem. 2008 Jan 21;6(2):391-6 - PubMed
  7. Biochemistry. 2005 Feb 22;44(7):2622-31 - PubMed
  8. Science. 1995 Jan 6;267(5194):90-3 - PubMed
  9. Biochemistry. 2009 Jun 23;48(24):5769-78 - PubMed
  10. J Am Chem Soc. 2002 Jul 17;124(28):8251-9 - PubMed
  11. Curr Opin Chem Biol. 2001 Dec;5(6):626-33 - PubMed
  12. J Am Chem Soc. 2010 May 26;132(20):7018-24 - PubMed
  13. J Exp Biol. 2003 Sep;206(Pt 17):2911-22 - PubMed
  14. Brookhaven Symp Biol. 1962 Dec;15:293-309 - PubMed
  15. J Am Chem Soc. 2001 Nov 14;123(45):11325-6 - PubMed
  16. J Am Chem Soc. 2010 Sep 29;132(38):13525-32 - PubMed
  17. Biochemistry. 2010 Sep 7;49(35):7704-8 - PubMed
  18. Chem Rev. 2005 Nov;105(11):4038-55 - PubMed
  19. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4046-50 - PubMed
  20. Proc Natl Acad Sci U S A. 2000 Feb 29;97(5):2011-6 - PubMed
  21. Biochemistry. 2007 May 15;46(19):5841-54 - PubMed
  22. J Am Chem Soc. 1986 Nov 1;108(24):7549-53 - PubMed
  23. J Mol Biol. 2002 Aug 30;321(5):741-65 - PubMed
  24. J Am Chem Soc. 2005 Nov 16;127(45):15708-9 - PubMed
  25. Biochemistry. 2005 Feb 22;44(7):2610-21 - PubMed
  26. Biochemistry. 2009 Aug 25;48(33):8006-13 - PubMed
  27. J Am Chem Soc. 2009 Oct 7;131(39):13952-62 - PubMed
  28. J Am Chem Soc. 2002 Nov 27;124(47):13986-7 - PubMed
  29. Biochemistry. 2010 Feb 9;49(5):824-6 - PubMed
  30. Acc Chem Res. 2001 Dec;34(12):981-8 - PubMed
  31. J Am Chem Soc. 2009 Oct 7;131(39):13963-71 - PubMed
  32. Philos Trans R Soc Lond B Biol Sci. 1991 May 29;332(1263):115-21 - PubMed
  33. Adv Enzymol Relat Areas Mol Biol. 1975;43:219-410 - PubMed
  34. Bioorg Chem. 2007 Aug;35(4):338-43 - PubMed
  35. J Am Chem Soc. 2007 Oct 31;129(43):12946-7 - PubMed
  36. Nature. 1948 May 8;161(4097):707-9 - PubMed
  37. Bioorg Chem. 2004 Oct;32(5):354-66 - PubMed
  38. J Am Chem Soc. 2002 Mar 27;124(12):2957-68 - PubMed
  39. Acc Chem Res. 2008 Apr;41(4):539-48 - PubMed
  40. Biochemistry. 2010 Jun 29;49(25):5377-89 - PubMed
  41. Biochemistry. 1976 Dec 14;15(25):5601-7 - PubMed

Publication Types

Grant support