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Videos de Conceptos Relacionados

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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Light-driven Enzymatic Decarboxylation
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La hidroperoxilación por el hidroxietilfosfonato de la dioxigenasa.

John T Whitteck1, Robert M Cicchillo, Wilfred A van der Donk

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Street, Urbana, Illinois 61801, USA.

Journal of the American Chemical Society
|October 21, 2009
PubMed
Resumen

La hidroxietilfosfonato dioxigenasa (HEPD) utiliza oxígeno molecular para dividir el 2-hidroxietilfosfonato (2-HEP). La enzima procede a través de la hidroperoxilación seguida de un reordenamiento de Criegee, no de la hidroxilación inicial.

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Área de la Ciencia:

  • La bioquímica es la bioquímica.
  • Enzimología Enzimología.
  • Biología Química Biología química.

Sus antecedentes:

  • La hidroxietilfosfonato dioxigenasa (HEPD) es una enzima que cataliza una escisión de enlace carbono-carbono dependiente de O2 única.
  • Se ha debatido el mecanismo de reacción de HEPD, con dos vías propuestas: hidroxilación inicial o hidroperoxilación inicial seguida de un reordenamiento Criegee.

Objetivo del estudio:

  • Para aclarar el mecanismo preciso de la hidroxietilfosfonato dioxigenasa (HEPD) en la división de 2-hidroxietilfosfonato (2-HEP).
  • Para distinguir entre las vías de reacción propuestas mediante la síntesis y prueba de análogos de sustrato.

Principales métodos:

  • Síntesis de análogos de sustratos, incluidos el hidroximetilfosfonato y el 1-hidroxietilfosfonato.
  • Ensayos enzimáticos utilizando análogos sintetizados para observar los productos de reacción.
  • Análisis de los productos de reacción para determinar la vía mecanicista.

Principales resultados:

  • El hidroximetilfosfonato fue convertido en fosfato y formato.
  • El 1-hidroxietilfosfonato dio lugar al acetilfosfato, un inhibidor de la enzima.
  • El (2R) -hidroxipropilfosfonato mostró una partición, produciendo 2-oxopropilfosfonato y hidroximetilfosfonato.

Conclusiones:

  • Los resultados apoyan fuertemente un mecanismo que implica la hidroperoxilación inicial del sustrato.
  • La reacción procede a través de un reordenamiento Criegee con un grupo migratorio basado en fósforo.
  • El enlace O-O del oxígeno molecular permanece intacto hasta la activación del sustrato.