Aqueous Synthesis of Peptide Thioesters from Amino Acids and a Thiol Using 1,1-Carbonyldiimidazole

Author: Weber, Arthur

Source: Origins of Life and Evolution of the Biosphere, Volume 35, Number 5, October 2005 , pp. 421-427(7)

Publisher: Springer

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Abstract:

A new method was developed for the synthesis of peptide thioesters from free amino acids and thiols in water. This one-pot simple method involves two steps: (1) activation in water of an amino acid presumably as its N-carboxyanhydride (NCA) using 1,1 prime

-carbonyldiimidazole (CDI), and (2) subsequent condensation of the activated amino acid-NCA in the presence of a thiol. With this method citrulline peptide thioesters containing up to 10 amino acid residues were prepared in a single reaction. This aqueous synthetic method provides a simple way to prepare peptide thioesters for studies of peptide replication involving ligation of peptide thioesters on peptide templates. The relevance of peptide replication to the origin-of-life process is supported by previous studies showing that amino acid thioesters (peptide thioester precursors) can be synthesized under prebiotic conditions by reaction of small sugars with ammonia and a thiol.

Keywords: aqueous thioester synthesis; carbonyldiimidazole; origin of life; peptide; peptide thioester; thioester

Document Type: Research article

DOI: http://dx.doi.org/10.1007/s11084-005-4070-0

Affiliations: 1: SETI Institute, Mail Stop 239-4, NASA Ames Research Center, Moffett Field, CA, 94035-1000, U.S.A., Email: aweber@mail.arc.nasa.gov

Publication date: 2005-10-01