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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Complexation Equilibria: The Chelate Effect01:19

Complexation Equilibria: The Chelate Effect

In complexation reactions, metal atoms or cations interact with ligands to form donor-acceptor adducts called metal complexes. Ligands that bind through one donor site are monodentate, ligands with two donor sites are bidentate, and those with more than two donor sites are polydentate ligands. For example, ethylene diamine is a bidentate ligand that binds through two nitrogen donor atoms, forming a five-membered ring. EDTA is a polydentate ligand that binds through four oxygen and two nitrogen...

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Sedimentation Equilibrium of a Small Oligomer-forming Membrane Protein: Effect of Histidine Protonation on Pentameric Stability
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Apparent NAC effect in chorismate mutase reflects electrostatic transition state stabilization.

Marek Strajbl1, Avital Shurki, Mitsunori Kato

  • 1Department of Chemistry, University of Southern California, Los Angeles, California 90098-1062, USA.

Journal of the American Chemical Society
|August 21, 2003
PubMed
Summary

Chorismate mutase (CM) primarily uses electrostatic transition state stabilization (TSS) for catalysis, not steric strain or near attack conformation (NAC). This electrostatic TSS explains the enzyme's catalytic power and influences reactant distances.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Computational Chemistry

Background:

  • Chorismate mutase (CM) is a key enzyme with significant catalytic activity.
  • The precise mechanism underlying CM's catalytic power, specifically the roles of electrostatic transition state stabilization (TSS), steric strain, and near attack conformation (NAC), remains incompletely understood.

Purpose of the Study:

  • To quantitatively analyze the catalytic mechanism of chorismate mutase (CM).
  • To determine whether CM utilizes electrostatic transition state stabilization (TSS), steric strain, or near attack conformation (NAC) as its primary catalytic strategy.
  • To elucidate the origin of CM's catalytic power.

Main Methods:

  • Empirical Valence Bond (EVB) method was employed to reproduce the overall catalytic effect.
  • Calculation of binding free energies for both the ground state and the transition state.
  • Evaluation of the electrostatic contribution to the reduction of activation energy.

Main Results:

  • The empirical valence bond (EVB) method successfully reproduced the catalytic effect of chorismate mutase (CM).
  • Analysis demonstrated that CM functions through electrostatic transition state stabilization (TSS), supported by binding free energy calculations.
  • The observed near attack conformation (NAC) effect was identified as a consequence, not a cause, of TSS.

Conclusions:

  • The primary catalytic mechanism of chorismate mutase (CM) is electrostatic transition state stabilization (TSS).
  • Electrostatic effects are the driving force behind the reduction in activation energy observed in CM catalysis.
  • Similar charge distributions between the transition and reactant states result in TSS, leading to a reduced interatomic distance in the reactant state.