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Related Concept Videos

Histone Modification02:32

Histone Modification

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The histone proteins have a flexible N-terminal tail extending out from the nucleosome. These histone tails are often subjected to post-translational modifications such as acetylation, methylation, phosphorylation, and ubiquitination. Particular combinations of these modifications form “histone codes” that influence the chromatin folding and tissue-specific gene expression.
Acetylation
The enzyme histone acetyltransferase adds acetyl group to the histones. Another enzyme, histone...
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Histone Modification02:32

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Protein Modifications in the RER01:26

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Modification of secretory and transmembrane proteins entering the rough ER begins in the ER lumen. These modifications aid in protein folding and stabilize the acquired tertiary structure. Protein modifications in the rough ER co-occur at different stages of protein folding.
Broadly, these modifications can be categorized into four main categories — glycosylation, formation of disulfide bonds, assembly of protein subunits, and specific proteolytic cleavages like removal of signal...
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Spreading of Chromatin Modifications02:25

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The histone proteins in the nucleosomes are post-translationally modified (PTM) to increase or decrease access to DNA. The commonly observed PTMs are methylation, acetylation, phosphorylation, and ubiquitination of lysine amino acids in the histone H3 tail region. These histone modifications have specific meaning for the cell. Hence, they are called "histone code". The protein complex involved in histone modification is termed as "reader-writer" complex.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Related Experiment Video

Updated: Feb 14, 2026

Quantification of Site-specific Protein Lysine Acetylation and Succinylation Stoichiometry Using Data-independent Acquisition Mass Spectrometry
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Quantification of Site-specific Protein Lysine Acetylation and Succinylation Stoichiometry Using Data-independent Acquisition Mass Spectrometry

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Chemo- and Regioselective Lysine Modification on Native Proteins.

Maria J Matos1, Bruno L Oliveira1, Nuria Martínez-Sáez1

  • 1Department of Chemistry , University of Cambridge , Lensfield Road , Cambridge , U.K.

Journal of the American Chemical Society
|February 24, 2018
PubMed
Summary

Computer-designed reagents enable precise modification of single lysine residues on native proteins. This advances protein conjugation for therapeutics and biological studies without genetic engineering.

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Area of Science:

  • Bioconjugation Chemistry
  • Protein Engineering
  • Chemical Biology

Background:

  • Protein modification is crucial for expanding therapeutic and functional applications.
  • Existing methods often require genetic modification or are limited to protein termini.
  • Site-selective conjugation remains a challenge in protein chemistry.

Purpose of the Study:

  • To develop a novel method for site-selective protein modification using computer-designed reagents.
  • To achieve modification of a single lysine residue on native protein sequences without engineering.
  • To demonstrate the utility of this method for creating functional protein conjugates.

Main Methods:

  • Computer-assisted design of sulfonyl acrylate reagents.
  • Utilizing inherent reactivity differences of lysine residues for regioselectivity.
  • Performing reactions under biocompatible conditions (37 °C, pH 8.0).

Main Results:

  • Successfully modified a single lysine residue on five different proteins, including the therapeutic antibody Trastuzumab.
  • Achieved site selectivity based on lysine pKa and local microenvironment, predicted computationally.
  • Demonstrated chemoselectivity for lysine over other nucleophiles like cysteine.
  • Created functional protein conjugates for cell imaging and diagnostics.

Conclusions:

  • The developed method offers a simple, robust, and non-genetic approach for site-selective protein modification.
  • This technology enables the creation of well-defined protein conjugates for diverse biological and therapeutic applications.
  • The regioselective lysine modification facilitates further bioconjugation for advanced applications.