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Related Concept Videos

Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H] allows...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...

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Related Experiment Video

Updated: May 29, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Unlocking a Nitrosuccinate Lyase for Decarboxylative Enzymatic Hydronitration.

Matteo Aleotti1, Hannah Dreisbach1, Rémi Corlay1

  • 1Institute of Chemistry, University of Graz, Graz, Austria.

Angewandte Chemie (International Ed. in English)
|May 28, 2026
PubMed
Summary

Researchers repurposed an enzyme for biocatalytic hydronitration, a novel method for synthesizing nitro compounds. This efficient enzymatic strategy offers a green chemistry approach for creating valuable chemical motifs.

Keywords:
biocatalysisenzymeshydronitrationmutagenesisreaction mechanisms

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Last Updated: May 29, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
06:00

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

Published on: January 15, 2018

Area of Science:

  • Biocatalysis
  • Synthetic Chemistry
  • Enzyme Engineering

Background:

  • Nitro compounds are essential in synthetic chemistry.
  • Mild and selective biocatalytic methods for nitro compound synthesis are lacking.
  • Enzymatic strategies offer potential for green chemistry approaches.

Purpose of the Study:

  • To develop a novel biocatalytic route for synthesizing nitro compounds.
  • To repurpose the nitrosuccinate lyase CreD for hydronitration.
  • To explore the efficiency and scope of this enzymatic strategy.

Main Methods:

  • Enzyme repurposing of nitrosuccinate lyase CreD.
  • Biocatalytic hydronitration using sodium nitrite.
  • Comprehensive mutagenesis and computational analysis.
  • QM/MM simulations for mechanism elucidation.

Main Results:

  • CreD and homologues efficiently catalyze hydronitration of fumarate.
  • High turnover numbers (up to 102,000) and atom economy were achieved.
  • Key molecular determinants for nucleophile selectivity and enzyme assembly were identified.
  • A diagnostic fingerprint for predicting hydronitration activity was defined.

Conclusions:

  • Enzymatic hydronitration is a viable and efficient biocatalytic strategy.
  • Repurposed enzymes offer a sustainable route to nitro compounds.
  • Molecular insights pave the way for expanding biocatalytic Michael-type additions.