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Formation of Amino Acid Thioesters for Prebiotic Peptide Synthesis: Catalysis By Amino Acid ProductsThe origin of life can be described as a series of events in which a prebiotic chemical process came increasingly under the control of its catalytic products. In our search for this prebiotic process that yielded catalytic takeover products (such as polypeptides), we have been investigating a reaction system that generates peptide-forming amino acid thioesters from formaldehyde, glycolaldehyde, and ammonia in the presence of thiols. As shown below, this model process begins by aldol condensation of formaldehyde and glycolaldehyde to give trioses and releases. These sugars then undergo beta-dehydration yielding their respective alpha-ketoaldehydes. Addition of ammonia to the alpha-ketoaldehydes yields imines which can either: (a) rearrange in the presence of thesis to give amino acid thioesters or (be react with another molecule of aldehyde to give imidazoles. This 'one-pot' reaction system operates under mild aqueous conditions, and like modem amino acid biosynthesis, uses sugar intermediates which are converted to products by energy-yielding redox reactions. Recently, we discovered that amino acids, such as the alanine reaction product, catalyze the first and second steps of the process. In the presence of ammonia the process also generates other synthetically useful products, like the important biochemical -- pyruvic acid.
Document ID
20020080720
Acquisition Source
Ames Research Center
Document Type
Abstract
Authors
Weber, Arthur L.
(Search for Extraterrestrial Intelligence Inst. Moffett Field, CA United States)
DeVincenzi, Donald L.
Date Acquired
August 20, 2013
Publication Date
January 1, 1999
Subject Category
Chemistry And Materials (General)
Meeting Information
Meeting: 12th International Conference on the Origin of Life
Location: San Diego, CA
Country: United States
Start Date: July 11, 1999
End Date: July 16, 1999
Funding Number(s)
CONTRACT_GRANT: NCC2-1075
Distribution Limits
Public
Copyright
Work of the US Gov. Public Use Permitted.

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