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Alanine synthesis from glyceraldehyde and ammonium ion in aqueous solutionThe formation of alanine (ala) form C(14)-glyceraldehyde and ammonium phosphate in the presence or absence of a thiol is reported. At ambient temperature, ala synthesis was six times more rapid in the presence of 3-mercaptopropionic acid than in its absence (0.6 and 0.1 percent, respectively, after 60 days). Similarly, the presence of another thiol, N-acetylcysteinate, increased the production of ala, as well as of lactate. The reaction pathway of thiol-catalyzed synthesis of ala, with the lactic acid formed in a bypath, is suggested. In this, dehydration of glyceraldehyde is followed by the formation of hemithioacetal. In the presence of ammonia, an imine is formed, which eventually yields ala. This pathway is consistent with the observation that the rate ratio of ala/lactate remains constant throughout the process. The fact that the reaction takes place under anaerobic conditions in the presence of H2O and with the low concentrations of simple substrates and catalysts makes it an attractive model prebiotic reaction in the process of molecular evolution.
Document ID
Document Type
Reprint (Version printed in journal)
External Source(s)
Weber, A. L.
(Salk Institute for Biological Studies San Diego, CA, United States)
Date Acquired
August 12, 2013
Publication Date
January 1, 1985
Publication Information
Publication: Journal of Molecular Evolution
Volume: 21
Issue: 4 19
ISSN: 0022-2844
Subject Category
Space Biology
Accession Number
Funding Number(s)
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