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Related Concept Videos

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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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Updated: Jul 16, 2026

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

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Published on: February 16, 2018

An Engineered Enzyme Catalyzing Tandem Reductive Aminations for Synthesizing Tertiary Amines.

Yaqing Ma1,2, Han Zhang1,3, Jinping Bao1,2

  • 1State Key Laboratory of Engineering Biology For Low-Carbon Manufacturing, Chinese Academy of Sciences, Tianjin Institute of Industrial Biotechnology, Tianjin, China.

Angewandte Chemie (International Ed. in English)
|July 15, 2026
PubMed
Summary

Researchers engineered a novel tandem aminase enzyme for sustainable, one-pot synthesis of diverse tertiary amines. This biocatalytic approach offers precise stereochemical control, addressing a key challenge in medicinal chemistry.

Keywords:
biocatalysisimine reductasestereoselectivitytandem aminasetertiary amines

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Area of Science:

  • Biocatalysis and Enzyme Engineering
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Tertiary amines are crucial structural motifs in many bioactive molecules.
  • Current chemical synthesis methods for tertiary amines often lack sustainability.
  • Biocatalytic routes for synthesizing tertiary amines are underdeveloped.

Purpose of the Study:

  • To develop innovative and sustainable catalytic strategies for tertiary amine synthesis.
  • To engineer a novel biocatalyst capable of efficient and stereoselective tertiary amine production.

Main Methods:

  • Engineering a wild-type imine reductase into a tandem aminase (AHTanAm) for consecutive intermolecular reductive aminations.
  • Utilizing X-ray crystallography and mutagenesis for mechanistic dissection of enzyme activity.
  • Demonstrating one-pot synthesis of a wide range of tertiary amines from primary amine precursors.

Main Results:

  • The engineered tandem aminase (AHTanAm) enables the one-pot synthesis of hundreds of tertiary amines.
  • The biocatalyst exhibits precise stereochemical control over multiple stereocenters.
  • Enzyme-pocket alterations were identified as key to amplifying the second-step amination activity, driving tandem catalysis.

Conclusions:

  • This study presents the first engineered tandem aminase for tertiary amine synthesis via imine reductase redesign.
  • The developed biocatalyst offers a sustainable and stereoselective alternative to traditional chemical synthesis.
  • This work addresses a critical synthetic challenge, providing access to valuable tertiary amine compounds.