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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
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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.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Información estructural sobre la preferencia del sustrato para la oxidación mediada por TET

Lulu Hu1,2,3, Junyan Lu4, Jingdong Cheng1,2

  • 1Fudan University Shanghai Cancer Center, Institute of Biomedical Sciences, Shanghai Medical College of Fudan University, Shanghai 200032, China.

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|November 3, 2015
PubMed
Resumen

Diez y once proteínas de translocación (TET) oxidan la metilación del ADN. TET1 y TET2 muestran una mayor actividad sobre la 5-metilcitocina (5mC) que la 5-hidroximetilcitocina (5hmC) o la 5-formilcitocina (5fC) debido a la conformación del sustrato y la eficiencia de la oxidación. Esto sugiere que 5hmC es una marca epigenética estable.

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Área de la Ciencia:

  • La epigenética
  • Biología molecular
  • La bioquímica

Sus antecedentes:

  • La metilación del ADN es un regulador epigenético clave.
  • Las proteínas de translocación diez-once (TET) median la desmetilación del ADN mediante la oxidación de la 5-metilcitosina (5mC).
  • Las proteínas TET convierten iterativamente 5mC en 5-hidroximetilcitocina (5hmC), 5-formilcitocina (5fC) y 5-carboxilcitocina (5caC).

Objetivo del estudio:

  • Investigar la preferencia de sustrato de las proteínas humanas TET1 y TET2.
  • Aclarar la base estructural de la actividad de la proteína TET en diferentes derivados de la metilación del ADN.
  • Comprender las implicaciones de la actividad de la proteína TET para la estabilidad de 5hmC como marca epigenética.

Principales métodos:

  • Determinación de las estructuras cristalinas de los complejos TET2-5hmC-DNA y TET2-5fC-DNA.
  • Análisis bioquímicos de la actividad de la proteína TET y la eficiencia de la oxidación del sustrato.
  • Análisis estructural comparativo de los complejos TET2-ADN con sustratos 5mC, 5hmC y 5fC.

Principales resultados:

  • Los TET1 y TET2 humanos muestran una mayor actividad enzimática en el ADN 5mC en comparación con el ADN 5hmC y el ADN 5fC.
  • Las estructuras cristalinas revelan una unión similar de 5mC, 5hmC y 5fC dentro de la cavidad catalítica TET2, pero con orientaciones distintas de las bases modificadas.
  • Los datos bioquímicos indican que las conformaciones restringidas de 5hmC y 5fC dificultan la abstracción eficiente de hidrógeno, lo que lleva a una menor eficiencia catalítica para estos sustratos.

Conclusiones:

  • La preferencia del sustrato de la proteína TET está determinada por las propiedades intrínsecas de los derivados de 5mC, específicamente la conformación y el potencial de enlace de hidrógeno de la base de citosina modificada.
  • La reactividad reducida de las proteínas TET hacia 5hmC sugiere que es una marca epigenética relativamente estable.
  • Las proteínas TET están evolutivamente optimizadas para generar y mantener 5hmC, potencialmente para diversas funciones reguladoras.