Prebiotic synthesis of histidine

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.

Possible prebiotic significance of polyamines in the condensation, protection, encapsulation, and biological properties of DNA

“…Preliminary studies in our laboratory suggest that ornithine can be obtained by heating L-arginine at temperatures below 100 °C, and several laboratories are pursuing the prebiotic synthesis of basic amino acids including arginine, and in regard to another basic amino acid Shen et al (1990) were able to demonstrate the prebiotic synthesis of histidine.…”

Molecular evolution of the histidine biosynthetic pathway

“…The name hisBd (limauro et al 1990) refers to genes coding an IGP dehydratase corresponding to the distal moiety of the enterobacterial HisB enzyme b Truncated genes or ORF of the metabolic abilities of the last common ancestor of the three extant cell domains (Lazcano et al 1992). The chemical syntheses of histidine (Shen et al 1990b) and prebiotic analogues of histidine (Maurel and Ninio 1987) and of histidyl-histidine under primitive conditions have been reported (Shen et al 1990a), as well as the role of the latter in the enhancement of some possible prebiotic oligomerization reactions involving amino acids (White and Erickson 1980) and nucleotides (Shen et al 1990c). Since its biosynthesis requires a carbon and a nitrogen equivalent from the purine ring of ATP, it has also been suggested that histidine may be the molecular vestige of a catalytic ribonucleotide from an earlier biochemical stage in which RNA played a major role in catalysis (White 1976).…”

Marine Hydrothermal Systems and the Origin of Life

“…These oligomers are not polypeptides since the amino acids formed constitute a small percent of the starting oligomers . Amino acids are also formed by the pyrolysis of formamide (Harada, 1967) and in reaction sequences starting from the sugars glucose or erythrose or from malic acid (Shen et al, 1987(Shen et al, , 1990. Amino acids are produced in small amounts in FTT reactions of CO, D2 and ND3 over meteoritic iron or iron oxide or montmorillonite and alumina at 200-1000°C (Yoshino et ai., 1971;Hayatsu et al, 1971).…”

“…Reaction of formamidine, the NH3 adduct of HeN, with erythrose yields imidazole-4-acetaldehyde (IAA). Histidine results when the amino nitrile derivative of IAA is hydrolyzed (equation 29) (Shen et al, 1987(Shen et al, , 1990. …”