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Videos de Conceptos Relacionados

Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Hidrólisis de amida catalizada por el ADN

Cong Zhou1, Joshua L Avins1, Paul C Klauser1

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|February 9, 2016
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron nuevos catalizadores de ADN (deoxiribozimas) para la hidrólisis de amida mediante la incorporación de grupos funcionales similares a las proteínas. Este avance permite la creación de proteasas artificiales para nuevas aplicaciones bioquímicas.

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Área de la Ciencia:

  • La bioquímica
  • Biología molecular
  • Biología sintética

Sus antecedentes:

  • Los catalizadores de ADN, o desoxiribozimas, son herramientas poderosas para diversas reacciones químicas.
  • La identificación de desoxiribozimas para la hidrólisis de amida ha sido un desafío, ya que los intentos anteriores arrojaron diferentes actividades catalíticas.

Objetivo del estudio:

  • Desarrollar desoxiribozimas capaces de catalizar la hidrólisis de las amidas alifáticas.
  • Explorar el uso de nucleótidos modificados con grupos funcionales similares a las proteínas para expandir las capacidades de la desoxiribozima.

Principales métodos:

  • Se utilizó la selección in vitro para identificar nuevas desoxiribozimas.
  • Se incorporaron nucleótidos modificados con grupos amino, carboxilo o hidroxilo primarios en las secuencias de ADN.
  • Las estrategias de selección se diseñaron para dirigirse específicamente a la hidrólisis de amida sobre la hidrólisis de fosfodiéster.

Principales resultados:

  • La incorporación de nucleótidos modificados permitió con éxito la identificación de desoxiribozimas amida-hidrolizantes.
  • Una desoxiribozima identificada mantuvo una actividad catalítica significativa incluso sin las modificaciones de nucleótidos.
  • El estudio demostró la eficacia de los grupos funcionales similares a las proteínas en el descubrimiento de nuevas funciones catalíticas para las desoxiribozimas.

Conclusiones:

  • Los nucleótidos modificados con grupos funcionales similares a las proteínas son cruciales para la identificación de desoxiribozimas amida-hidrolizantes.
  • Estos hallazgos destacan el potencial de las desoxiribozimas como proteasas artificiales para futuras aplicaciones.
  • La estrategia de incorporar grupos funcionales puede aplicarse para descubrir otras actividades novedosas de la desoxiribozima.