Reaction of Nα-acetyl-L-histidine with diazomethane: A model esterification reaction of carboxylic groups in the presence of imidazole rings

Authors

  • R. Zamora Instituto de la Grasa, CSIC
  • F. J. Hidalgo Instituto de la Grasa, CSIC

DOI:

https://doi.org/10.3989/gya.1996.v47.i5.876

Keywords:

Diazomethane, Imidazole methylation, Capillary electrophoresis, Oxidized lipid/amino acid reaction products

Abstract


The reaction of Nα-acetyl-L-histidine with diazomethane was studied in order to analyze the esterification reaction of a carboxylic group in the presence of an imidazole ring. The reaction produced the expected Nα-acetyl-L-histidine methyl ester (1) as a major product. However, important amounts of [S]-acetyl-1-methylimidazole-4-alanine methyl ester (2) and [S]-acetyl-1-methylimidazole-5-alanine methyl ester (3) were also produced. These compounds, which could be detected by capillary electrophoresis (HPCE) and thin layer chromatography, were fractionated by column chromatography and identified by gas chromatography coupled with mass spectrometry (GC-MS), and 1H and 13C nuclear magnetic resonance spectroscopy. Structures for compounds 1-3 were confirmed by HPCE after acid hydrolysis. These results indicated that the use of diazomethane produces the methyl derivative of the heterocyclic ring in addition to the methyl ester. This reaction should be considered when preparing derivatives for GC-MS analysis.

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Published

1996-10-30

How to Cite

1.
Zamora R, Hidalgo FJ. Reaction of Nα-acetyl-L-histidine with diazomethane: A model esterification reaction of carboxylic groups in the presence of imidazole rings. Grasas aceites [Internet]. 1996Oct.30 [cited 2024Feb.28];47(5):326-30. Available from: https://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/876

Issue

Section

Research

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