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Reactions of aminomalononitrile with electrophiles

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Summary

Aminomalononitrile (HCN trimer) reacts with electrophiles such as aldehydes and acrylonitrile under very mild conditions of temperature and pH to produce intermediates which, after acid hydrolysis, yield amino acids. The following amino acids have been identified and quantitated: glycine, D, L-erythro- and D, L-threo-ß - hydroxyaspartic acids, D, L glutamic acid, and D, L-threonine and allo-threonine. The mechanism of their formation and the possible significance of these reactions in prebiotic syntheses are discussed.

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Authors and Affiliations

  1. The Salk Institute for Biological Studies, San Diego, USA

    John W. Thanassi

  2. Department of Biochemistry, University of Vermont College of Medicine, 05401, Burlington, Vermont, USA

    John W. Thanassi

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  1. John W. Thanassi
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Thanassi, J.W. Reactions of aminomalononitrile with electrophiles. J Mol Evol 7, 65–73 (1975). https://doi.org/10.1007/BF01732180

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  • DOI: https://doi.org/10.1007/BF01732180

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