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Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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A method for concurrent diazomethane synthesis and substrate methylation in a 96-sample format.

Lana S Barkawi1, Jerry D Cohen

  • 1Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, Saint Paul, USA.

Nature Protocols
|October 2, 2010
PubMed
Summary

This study presents a safe, in situ method for methylating organic acids using diazomethane in a 96-sample format. This protocol enhances metabolomics workflows by enabling rapid derivatization for gas chromatography-mass spectrometry analysis.

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Area of Science:

  • Analytical Chemistry
  • Metabolomics
  • Biochemistry

Background:

  • Metabolomics requires efficient sample derivatization for gas chromatography-mass spectral (GC-MS) analysis.
  • Current methods face challenges with large sample numbers and the hazardous nature of reagents like diazomethane.
  • There is a need for improved, safer derivatization protocols in high-throughput metabolomics.

Purpose of the Study:

  • To develop and detail a safe, direct derivatization protocol for organic acids using diazomethane.
  • To adapt the derivatization process for a 96-sample format suitable for high-throughput analysis.
  • To minimize risks associated with diazomethane handling and storage.

Main Methods:

  • In situ generation and concurrent use of diazomethane for methylation of carboxylic acid functionalities.
  • A 96-sample format protocol for simultaneous derivatization.
  • Gas chromatographic-mass spectral (GC-MS) analysis of derivatized organic acids.

Main Results:

  • Diazomethane readily forms methyl esters with carboxylic acids, yielding minimal side products.
  • The in situ generation and concurrent use obviates the need for storing hazardous diazomethane solutions.
  • Processing up to 96 samples takes only 2-3 hours after generator assembly.

Conclusions:

  • This protocol offers a safe and efficient method for the derivatization of organic acids in metabolomics.
  • The 96-sample format significantly improves throughput for GC-MS based metabolite analysis.
  • In situ diazomethane generation enhances safety and simplifies the workflow for large-scale metabolomic studies.