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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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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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Video Experimental Relacionado

Updated: Feb 14, 2026

Quantification of Site-specific Protein Lysine Acetylation and Succinylation Stoichiometry Using Data-independent Acquisition Mass Spectrometry
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Modificación de la lisina por quimioterapia y regioselectividad en proteínas nativas

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
Resumen

Los reactivos diseñados por ordenador permiten la modificación precisa de los residuos de lisina en las proteínas nativas. Esto hace avanzar la conjugación de proteínas para terapias y estudios biológicos sin ingeniería genética.

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Last Updated: Feb 14, 2026

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Área de la Ciencia:

  • Bioconjugación Química
  • Ingeniería de proteínas
  • Biología Química

Sus antecedentes:

  • La modificación de proteínas es crucial para ampliar las aplicaciones terapéuticas y funcionales.
  • Los métodos existentes a menudo requieren modificación genética o están limitados a los terminales de proteínas.
  • La conjugación selectiva del sitio sigue siendo un desafío en la química de las proteínas.

Objetivo del estudio:

  • Desarrollar un nuevo método para la modificación selectiva de proteínas utilizando reactivos diseñados por ordenador.
  • Para lograr la modificación de un solo residuo de lisina en secuencias de proteínas nativas sin ingeniería.
  • Demostrar la utilidad de este método para crear conjugados de proteínas funcionales.

Principales métodos:

  • Diseño asistido por ordenador de reactivos de acrilato de sulfonilo.
  • Utilizando las diferencias de reactividad inherentes de los residuos de lisina para la regioselectividad.
  • Realización de reacciones en condiciones biocompatibles (37 °C, pH 8,0).

Principales resultados:

  • Modificó con éxito un solo residuo de lisina en cinco proteínas diferentes, incluido el anticuerpo terapéutico Trastuzumab.
  • Se ha logrado una selectividad del sitio basada en la lisina pKa y el microambiente local, predicha por computación.
  • Se ha demostrado la quimioselectividad de la lisina sobre otros nucleófilos como la cisteína.
  • Creado conjugados de proteínas funcionales para imágenes celulares y diagnósticos.

Conclusiones:

  • El método desarrollado ofrece un enfoque simple, robusto y no genético para la modificación de proteínas selectivas del sitio.
  • Esta tecnología permite la creación de conjugados de proteínas bien definidos para diversas aplicaciones biológicas y terapéuticas.
  • La modificación regioselectiva de la lisina facilita una mayor bioconjugación para aplicaciones avanzadas.