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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

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

Preparation of Amines: Reduction of Amides and Nitriles

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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,...
3.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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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,...
4.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.7K
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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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

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Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.8K
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...
4.8K

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Inhibition of Aspergillus flavus Growth and Aflatoxin Production in Transgenic Maize Expressing the &#945;-amylase Inhibitor from Lablab purpureus L.
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A reductive aminase from Aspergillus oryzae.

Godwin A Aleku1, Scott P France1, Henry Man2

  • 1School of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester M1 7DN, UK.

Nature Chemistry
|September 23, 2017
PubMed
Summary
This summary is machine-generated.

A novel Aspergillus oryzae enzyme, AspRedAm, efficiently catalyzes reductive amination for chiral amine synthesis. This NADP(H)-dependent biocatalyst achieves high conversion and enantiomeric excess for diverse substrates.

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Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
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Area of Science:

  • Biocatalysis and Enzyme Engineering
  • Organic Synthesis
  • Structural Biology

Background:

  • Reductive amination is crucial for synthesizing chiral amines, essential building blocks in pharmaceuticals.
  • Existing methods often face limitations in substrate scope, efficiency, or stereoselectivity.

Purpose of the Study:

  • To discover and characterize a novel enzyme for efficient reductive amination.
  • To explore the enzyme's catalytic mechanism and structural basis for activity.

Main Methods:

  • Discovery and heterologous expression of Aspergillus oryzae reductive aminase (AspRedAm).
  • Enzyme activity assays with various carbonyl compounds and amines.
  • Steady-state kinetic studies.
  • X-ray crystallography of AspRedAm in complex with NADP(H) and (R)-rasagiline.
  • Preparative scale reaction optimization.

Main Results:

  • AspRedAm demonstrates broad substrate scope, catalyzing reductive amination with >98% conversion and >98% enantiomeric excess.
  • Kinetic studies confirm the enzyme's ability to catalyze both imine formation and reduction.
  • Crystal structures reveal enzyme-cofactor and enzyme-cofactor-substrate interactions.
  • Preparative scale reactions achieved high total turnover numbers (up to 32,000) and space-time yields (up to 3.73 g/L/d).

Conclusions:

  • AspRedAm is a highly efficient and versatile biocatalyst for chiral amine synthesis.
  • Structural insights provide a foundation for further enzyme engineering.
  • The enzyme holds significant potential for industrial applications in pharmaceutical synthesis.