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Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Updated: Mar 7, 2026

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry

Published on: November 20, 2014

Solid-phase reductive amination for glycomic analysis.

Kuan Jiang¹, He Zhu², Cong Xiao²

¹State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300353, China; Department of Chemistry, Georgia State University, Atlanta, GA 30303, United States.

Analytica Chimica Acta

|February 25, 2017

Summary

This summary is machine-generated.

Solid-phase reductive amination simplifies glycan analysis by streamlining extraction, derivatization, and purification. This efficient method improves sample recovery and reproducibility for glycomic characterization.

Keywords:

Glycomic analysis Non-porous graphitized carbon Reductive amination Relative quantification Solid-phase strategy

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Last Updated: Mar 7, 2026

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry

Improved In-gel Reductive β-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry

Published on: November 20, 2014

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Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling

Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling

Published on: February 5, 2018

Area of Science:

Glycomics
Analytical Chemistry
Biochemistry

Background:

Reductive amination is crucial for glycan characterization and quantification.
Traditional in-solution methods are time-consuming and complex.

Purpose of the Study:

To develop a simpler and more efficient solid-phase reductive amination strategy for glycan analysis.
To streamline glycan extraction, derivatization, and purification processes.

Main Methods:

Investigated solid-phase reductive amination using non-porous graphitized carbon sorbents.
Tested neutral and sialylated glycans with aniline, 2-aminobenzamide (2-AB), 2-aminobenzoic acid (2-AA), and 2-amino-N-(2-aminoethyl)-benzamide (AEAB) labels.
Analyzed labeled glycans using High Performance Liquid Chromatography (HPLC) and Matrix Assisted Laser Desorption Ionization-Time of Flight Mass Spectrometry (MALDI-TOF MS).

Main Results:

Achieved near-complete labeling of glycans with minimal desialylation.
Demonstrated excellent reproducibility in HPLC and MALDI-TOF MS analyses.
Showed a 20-30% increase in sample recovery compared to traditional methods.
Successfully applied to N-glycan profiling of HEK 293 cells.

Conclusions:

Solid-phase reductive amination is a simple, reproducible, efficient, and sensitive method for glycan analysis.
This strategy enhances sample recovery and is suitable for high-throughput mammalian glycome analysis.