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Literature DB >> 15450493

Enzymatic reactions involving novel mechanisms of carbanion stabilization.

Abstract

The reactions catalyzed by orotidine monophosphate decarboxylase, oxalate decarboxylase, organomercurial lyase and phosphopantothenoylcysteine decarboxylase involve putative high-energy carbanion intermediates that cannot be stabilized by delocalization. Mechanistic and structural studies on each of these enzymes are described that suggest different strategies for carbanion stabilization. Both orotidine monophosphate decarboxylase and organomercurial lyase are likely to avoid carbanion formation by protonating the fragmenting bond, oxalate decarboxylase stabilizes an acyl carbanion using an adjacent radical and phosphopantothenoylcysteine decarboxylase stabilizes its carbanion by delocalization into a transient thioaldehyde.

Entities: Chemical

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Year: 2004 PMID： 15450493 DOI： 10.1016/j.cbpa.2004.08.004

Source DB: PubMed Journal: Curr Opin Chem Biol ISSN： 1367-5931 Impact factor: 8.822

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Cited

19 in total

1. Product deuterium isotope effects for orotidine 5'-monophosphate decarboxylase: effect of changing substrate and enzyme structure on the partitioning of the vinyl carbanion reaction intermediate.

Authors: Krisztina Toth; Tina L Amyes; Bryant M Wood; Kui Chan; John A Gerlt; John P Richard
Journal: J Am Chem Soc Date: 2010-05-26 Impact factor: 15.419

2. Product deuterium isotope effect for orotidine 5'-monophosphate decarboxylase: evidence for the existence of a short-lived carbanion intermediate.

Authors: Krisztina Toth; Tina L Amyes; Bryant M Wood; Kui Chan; John A Gerlt; John P Richard
Journal: J Am Chem Soc Date: 2007-10-05 Impact factor: 15.419

3. The identity of the active site of oxalate decarboxylase and the importance of the stability of active-site lid conformations.

Authors: Victoria J Just; Matthew R Burrell; Laura Bowater; Iain McRobbie; Clare E M Stevenson; David M Lawson; Stephen Bornemann
Journal: Biochem J Date: 2007-11-01 Impact factor: 3.857

4. Electronic structure of the Mn-cofactor of modified bacterial reaction centers measured by electron paramagnetic resonance and electron spin echo envelope modulation spectroscopies.

Authors: A A Tufts; M Flores; T L Olson; J C Williams; J P Allen
Journal: Photosynth Res Date: 2013-07-19 Impact factor: 3.573

5. Proton transfer from C-6 of uridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase: formation and stability of a vinyl carbanion intermediate and the effect of a 5-fluoro substituent.

Authors: Wing-Yin Tsang; B McKay Wood; Freeman M Wong; Weiming Wu; John A Gerlt; Tina L Amyes; John P Richard
Journal: J Am Chem Soc Date: 2012-08-21 Impact factor: 15.419

10. An examination of the relationship between active site loop size and thermodynamic activation parameters for orotidine 5'-monophosphate decarboxylase from mesophilic and thermophilic organisms.

Authors: Krisztina Toth; Tina L Amyes; B McKay Wood; Kui K Chan; John A Gerlt; John P Richard
Journal: Biochemistry Date: 2009-08-25 Impact factor: 3.162

Enzymatic reactions involving novel mechanisms of carbanion stabilization.

1. Product deuterium isotope effects for orotidine 5'-monophosphate decarboxylase: effect of changing substrate and enzyme structure on the partitioning of the vinyl carbanion reaction intermediate.

2. Product deuterium isotope effect for orotidine 5'-monophosphate decarboxylase: evidence for the existence of a short-lived carbanion intermediate.

3. The identity of the active site of oxalate decarboxylase and the importance of the stability of active-site lid conformations.

4. Electronic structure of the Mn-cofactor of modified bacterial reaction centers measured by electron paramagnetic resonance and electron spin echo envelope modulation spectroscopies.

5. Proton transfer from C-6 of uridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase: formation and stability of a vinyl carbanion intermediate and the effect of a 5-fluoro substituent.

6. Primary Deuterium Kinetic Isotope Effects From Product Yields: Rationale, Implementation, and Interpretation.

7. Structural basis of hereditary coproporphyria.

8. Photoactivation mechanism of PAmCherry based on crystal structures of the protein in the dark and fluorescent states.

9. Investigating the roles of putative active site residues in the oxalate decarboxylase from Bacillus subtilis.

10. An examination of the relationship between active site loop size and thermodynamic activation parameters for orotidine 5'-monophosphate decarboxylase from mesophilic and thermophilic organisms.