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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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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.
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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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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
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.1K
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,...
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Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

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Oxidation–Reduction Reactions
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Updated: Feb 14, 2026

Sample Preparation and Relative Quantitation using Reductive Methylation of Amines for Peptidomics Studies
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Sample Preparation and Relative Quantitation using Reductive Methylation of Amines for Peptidomics Studies

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Quantitative Peptidomics Using Reductive Methylation of Amines.

Sayani Dasgupta1, Leandro M Castro2, Alexandre K Tashima3

  • 1Department of Molecular Pharmacology, Albert Einstein College of Medicine, Bronx, NY, USA.

Methods in Molecular Biology (Clifton, N.J.)
|February 25, 2018
PubMed
Summary
This summary is machine-generated.

This study introduces a novel quantitative peptidomics method using formaldehyde and sodium cyanoborohydride for amine methylation. This approach enables precise peptide quantification via mass spectrometry using five isotopically distinct forms.

Keywords:
CyanoborohydrideFormaldehydeIsotopic labels

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

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Quantitative Proteomics Using Reductive Dimethylation for Stable Isotope Labeling
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Sample Preparation and Relative Quantitation using Reductive Methylation of Amines for Peptidomics Studies
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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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Quantitative Proteomics Using Reductive Dimethylation for Stable Isotope Labeling
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Quantitative Proteomics Using Reductive Dimethylation for Stable Isotope Labeling

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Area of Science:

  • Biochemistry
  • Analytical Chemistry
  • Proteomics

Background:

  • Quantitative peptidomics is crucial for biological research.
  • Existing methods for peptide quantification have limitations.
  • Amine modification is a common strategy in quantitative proteomics.

Purpose of the Study:

  • To describe a new protocol for quantitative peptidomics.
  • To enable precise quantification of peptides using mass spectrometry.
  • To develop a cost-effective and stable method for peptide analysis.

Main Methods:

  • Peptides are reacted with formaldehyde and sodium cyanoborohydride to methylate primary and secondary amines.
  • Isotopically distinct reagents (deuterated and 13C-containing) are used to generate five forms of methylated peptides.
  • Mass spectrometry is employed for the quantification of these distinct peptide forms.

Main Results:

  • The method allows for the generation of five isotopically distinct methylated peptide forms.
  • N-terminal primary amines incorporate two methyl groups, creating a 2 Da mass difference per isotopic form.
  • Unmodified lysine residues lead to additional methylations, resulting in larger mass differences between isotopic forms.

Conclusions:

  • This formaldehyde-based methylation protocol offers a robust method for quantitative peptidomics.
  • The use of isotopically distinct reagents allows for sensitive and accurate peptide quantification.
  • The reagents are readily available, inexpensive, and stable, making the method accessible.