Prebiotic synthesis of histidine

J Mol Evol. 1990 Sep;31(3):167-74. doi: 10.1007/BF02109492.

Abstract

The prebiotic formation of histidine (His) has been accomplished experimentally by the reaction of erythrose with formamidine followed by a Strecker synthesis. In the first step of this reaction sequence, the formation of imidazole-4-acetaldehyde took place by the condensation of erythrose and formamidine, two compounds that are known to be formed under prebiotic conditions. In a second step, the imidazole-4-acetaldehyde was converted to His, without isolation of the reaction products by adding HCN and ammonia to the reaction mixture. LC, HPLC, thermospray liquid chromatography-mass spectrometry, and tandem mass spectrometry were used to identify the product, which was obtained in a yield of 3.5% based on the ratio of His/erythrose. This is a new chemical synthesis of one of the basic amino acids which had not been synthesized prebiotically until now.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes
  • Amidines / chemistry
  • Ammonia / chemistry
  • Evolution, Chemical*
  • Evolution, Molecular*
  • Histidine / chemical synthesis*
  • Hydrogen Cyanide / chemistry
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Tetroses / chemistry

Substances

  • Aldehydes
  • Amidines
  • Imidazoles
  • Tetroses
  • Hydrogen Cyanide
  • formamidine
  • Histidine
  • 1H-imidazole-4-acetaldehyde
  • Ammonia
  • erythrose