Reaction of beta-propiolactone with amino acids and its specificity for methionine

Biochem J. 1968 Feb;106(4):829-34. doi: 10.1042/bj1060829.

Abstract

1. The reactions of beta-propiolactone with amino acids were investigated under various conditions of pH and temperature to find those under which the reagent acted with specificity. 2. At pH9.0 and 22 degrees , after 15min. of reaction, at least 85% of each amino acid had reacted, methionine and cystine being the most reactive. 3. At pH7.0 and 22 degrees most amino acids reacted; methionine, cystine and histidine reacted almost entirely, and proline and lysine to a significantly smaller extent. 4. At pH3.0 and 22 degrees further specificity was obtained; methionine and cystine were the only reactive amino acids. 5. Reaction at pH3.0 and 0 degrees was specific for methionine; it was the only amino acid modified even after 145hr. of reaction.

MeSH terms

  • Amino Acids*
  • Autoanalysis
  • Chemical Phenomena
  • Chemistry
  • Cold Temperature
  • Cystine
  • Histidine
  • Hydrogen-Ion Concentration
  • Isoleucine
  • Lactones*
  • Leucine
  • Lysine
  • Methionine*
  • Phenylalanine
  • Proline
  • Tyrosine

Substances

  • Amino Acids
  • Lactones
  • Isoleucine
  • Tyrosine
  • Phenylalanine
  • Cystine
  • Histidine
  • Proline
  • Methionine
  • Leucine
  • Lysine