Analysis of cyclic pyrolysis products formed from amino acid monomer

J Chromatogr A. 2011 Nov 18;1218(46):8443-55. doi: 10.1016/j.chroma.2011.09.055. Epub 2011 Sep 24.

Abstract

Amino acid was mixed with silica and tetramethylammonium hydroxide (TMAH) to favor pyrolysis of amino acid monomer. The pyrolysis products formed from amino acid monomer were using GC/MS and GC. 20 amino acids of alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine were analyzed. The pyrolysis products were divided into cyclic and non-cyclic products. Among the 20 amino acids, arginine, asparagine, glutamic acid, glutamine, histidine, lysine, and phenylalanine generated cyclic pyrolysis products of the monomer. New cyclic pyrolysis products were formed by isolation of amino acid monomers. They commonly had polar side functional groups to 5-, 6-, or 7-membered ring structure. Arginine, asparagine, glutamic acid, glutamine, histidine, and phenylalanine generated only 5- or 6-membered ring products. However, lysine generated both 6- and 7-membered ring compounds. Variations of the relative intensities of the cyclic pyrolysis products with the pyrolysis temperature and amino acid concentration were also investigated.

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids, Cyclic
  • Chemical Phenomena
  • Gas Chromatography-Mass Spectrometry / methods*
  • Hot Temperature
  • Molecular Conformation
  • Quaternary Ammonium Compounds
  • Silicon Dioxide

Substances

  • Amino Acids
  • Amino Acids, Cyclic
  • Quaternary Ammonium Compounds
  • Silicon Dioxide
  • tetramethylammonium