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E2 Reaction: Stereochemistry and Regiochemistry

E2 Reaction: Stereochemistry and Regiochemistry

Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...

Mismatch Repair

Mismatch Repair

Organisms are capable of detecting and fixing nucleotide mismatches that occur during DNA replication. This sophisticated process requires identifying the new strand and replacing the erroneous bases with correct nucleotides. Mismatch repair is coordinated by many proteins in both prokaryotes and eukaryotes.
The Mutator Protein Family Plays a Key Role in DNA Mismatch Repair
The human genome has more than 3 billion base pairs of DNA per cell. Prior to cell division, that vast amount of genetic...

Mismatch Repair

Mismatch Repair

E1 Reaction: Stereochemistry and Regiochemistry

E1 Reaction: Stereochemistry and Regiochemistry

One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.

E2 Reaction: Kinetics and Mechanism

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...

Position-effect Variegation

Position-effect Variegation

In 1928, a German botanist Emil Heitz observed the moss nuclei with a DNA binding dye. He observed that while some chromatin regions decondense and spread out in the interphase nucleus, others do not. He termed them euchromatin and heterochromatin, respectively. He proposed that the heterochromatin regions reflect a functionally inactive state of the genome. It was later confirmed that heterochromatin is transcriptionally repressed, and euchromatin is transcriptionally active chromatin.

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Related Experiment Video

Updated: Jul 10, 2026

A Method to Study de novo Formation of Chromatin Domains

A Method to Study de novo Formation of Chromatin Domains

Published on: August 23, 2019

Structural basis of EZH2 recognition by EED.

Zhifu Han¹, Xinmiao Xing, Min Hu

¹National Institute of Biological Sciences, Beijing 102206, China.

Structure (London, England : 1993)

|October 17, 2007

Summary

This study reveals the crystal structure of EED bound to an EZH2 peptide, showing how WD-repeat domains recognize partners. This finding offers insights into protein interactions within the PRC2 complex and gene repression mechanisms.

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Area of Science:

Biochemistry
Molecular Biology
Structural Biology

Background:

WD-repeat domains are crucial eukaryotic recognition modules.
The precise mechanism of WD-repeat domain partner recognition, particularly at the domain's base, remains unclear.
EED, a WD-repeat protein, is a key component of the Polycomb Repressive Complex 2 (PRC2), essential for gene silencing via histone methylation.

Purpose of the Study:

To elucidate the structural basis of the interaction between the WD-repeat protein EED and its binding partner EZH2.
To understand how the bottom of a WD-repeat domain recognizes its cognate peptide.

Main Methods:

X-ray crystallography was employed to determine the structure of EED in complex with a 30-residue peptide from EZH2.
Structure-based mutagenesis was utilized to identify critical residues involved in the EZH2-EED interaction.

Main Results:

The crystal structure reveals that the EZH2 peptide binds to the bottom surface of the EED WD-repeat domain.
Structural analysis indicates conserved recognition motifs in EZH2, EZH1, and the Drosophila homolog E(Z), suggesting conserved interaction mechanisms across species.
Key residues in both EED and EZH2 essential for their interaction were identified through mutagenesis.

Conclusions:

The determined structure provides a molecular template for understanding how WD-repeat proteins recognize their binding partners at the domain's base.
This work sheds light on the interaction dynamics within the PRC2 complex and its role in gene regulation.
The findings suggest evolutionary conservation in the recognition mechanisms involving EED and its homologs.