Prebiotic synthesis of histidine.
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.
Shen
C
C
Department of Biophysical and Biochemical Sciences, University of Houston, Texas 77204-5500, USA.
Yang
L
L
Miller
S L
SL
Oro
J
J
D000447:Aldehydes; D000578:Amidines / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry; D019418:Evolution, Chemical; D019143:Evolution, Molecular; D006639:Histidine / Q000138:chemical synthesis*; D006856:Hydrogen Cyanide / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D013780:Tetroses / Q000737:chemistry
D000447:Aldehydes; D000578:Amidines; D007093:Imidazoles; D013780:Tetroses; D006856:Hydrogen Cyanide; C077922:formamidine; D006639:Histidine; C053546:1H-imidazole-4-acetaldehyde; D000641:Ammonia; C073321:erythrose