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Prebiotic synthesis of histidine

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Summary

The prebiotic formation of histidine (His) has been accomplished experimentally by the reacton 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 has not been synthesized prebiotically until now.

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Author notes

  1. C. Shen

    Present address: Department of Biological Chemistry, Molecular Biology Institute, School of Medicine, University of California, Los Angeles, 90024, Los Angeles, California, USA

Authors and Affiliations

  1. Department of Biophysical and Biochemical Sciences, University of Houston, 77204-5500, Houston, Texas, USA

    C. Shen & J. Oró

  2. Department of Chemistry, University of Houston, 77204-5500, Houston, Texas, USA

    L. Yang

  3. De[artment of Chemistry, University of California, San Diego, 92093, La Jolla, California, USA

    S. L. Miller

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  1. C. Shen
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  2. L. Yang
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  3. S. L. Miller
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  4. J. Oró
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Shen, C., Yang, L., Miller, S.L. et al. Prebiotic synthesis of histidine. J Mol Evol 31, 167–174 (1990). https://doi.org/10.1007/BF02109492

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  • DOI: https://doi.org/10.1007/BF02109492

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