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Science 7 November 1969:
Vol. 166. no. 3906, pp. 766 - 767
DOI: 10.1126/science.166.3906.766
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Articles

Phenylalanine and Tyrosine Synthesis under Primitive Earth Conditions

Nadav Friedmann 1 and Stanley L. Miller 1

1 Department of Chemistry, University of California, San Diego, La Jolla 92037

Phenylacetylene can be synthesized in substantial yields from various hydrocarbons by high temperatures, electric discharges, and ultraviolet light. Phenylacetylene is hydrated to phenylacetaldehyde by way of both nucleophilic and radical additions of H2S followed by hydrolysis of the thtioaldehyde. The addition of NH3 and HCN to phenylacetaldehyde yields phenylalanine nitrile which is hydrolyzed to phenylalanine. A small yield of tyrosine is obtained from the radical addition of H2S to phenylacetylene. This sequence of reactions is a possible mechanism for the synthesis of these amino acids on the primitive earth.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Which Organic Compounds Could Have Occurred on the Prebiotic Earth?.
S.L. Miller (1987)
Cold Spring Harb Symp Quant Biol 52, 17-27
   Abstract »    PDF »
Primitive Earth Synthesis of Nicotinic Acid Derivatives.
N. Friedmann, S. L. Miller, and R. A. Sanchez (1971)
Science 171, 1026-1027
   Abstract »    PDF »


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Science. ISSN 0036-8075 (print), 1095-9203 (online)