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Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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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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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control01:23

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The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.
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Regioselectivity and Stereochemistry of Hydroboration02:36

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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...
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Efficient Purification and LC-MS/MS-based Assay Development for Ten-Eleven Translocation-2 5-Methylcytosine Dioxygenase
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Control de la transferencia de electrones en el metano soluble monooxigenasa.

Weixue Wang1, Roxana E Iacob, Rebecca P Luoh

  • 1Departments of †Chemistry and §Biological Engineering, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|June 18, 2014
PubMed
Resumen

Las monooxigenasas multicomponentes bacterianas (BMM) utilizan múltiples proteínas para la oxidación de hidrocarburos. Descubrimos que las proteínas reguladoras inhiben la unión de la reductasa, controlando la transferencia de electrones al sitio activo de la enzima.

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Área de la Ciencia:

  • La bioquímica es la bioquímica.
  • Enzimología Enzimología.
  • El metabolismo microbiano es el metabolismo microbiano.

Sus antecedentes:

  • Las monooxigenasas multicomponentes bacterianas (BMM) catalizan la hidroxilación/epoxidación de hidrocarburos a través de complejos de proteínas múltiples.
  • Las interacciones precisas entre los componentes de BMM y las funciones de las proteínas reguladoras en la transferencia de electrones siguen sin estar claras.

Objetivo del estudio:

  • Para dilucidar el sitio de unión de la reductasa en el componente hidroxilasa de la metano monooxigenasa soluble (sMMO).
  • Para investigar el papel de las proteínas reguladoras en la modulación de la transferencia de electrones intermoleculares en sMMO.

Principales métodos:

  • Cristalografía de rayos X o cryo-EM para determinar las estructuras de las proteínas.
  • Análisis bioquímicos para medir las tasas de transferencia de electrones.
  • Estudios de mutagenesis para sondear las interacciones proteína-proteína.

Principales resultados:

  • El dominio de ferredoxina de la reductasa se une a la región de cañón de la hidroxilasa.
  • Esta región del cañón es también el sitio de unión para las proteínas reguladoras.
  • Las proteínas reguladoras inhiben la unión de la reductasa, controlando así la transferencia de electrones.

Conclusiones:

  • Un mecanismo de unión competitivo entre las proteínas reguladoras y las reductasas regula la transferencia de electrones en sMMO.
  • Este mecanismo probablemente se extiende a otras monooxigenasas bacterianas multicomponentes.