Carbonyl sulfide-mediated synthesis of phosphate anhydrides and amino acid derivatives in water

ORGN 875

Luke J. Leman, lleman@scripps.edu1, Leslie E. Orgel, orgel@salk.edu2, and M. Reza Ghadiri, ghadiri@scripps.edu1. (1) Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, (2) The Salk Institute for Biological Studies, PO Box 85800, San Diego, CA 92186
Carbonyl sulfide (COS), a component of volcanic gas emissions and interstellar gas clouds, brings about the formation of peptides from amino acids efficiently under mild aqueous conditions. Here we describe experiments demonstrating that, in addition to peptide synthesis, COS can also mediate amino acid dependent phosphorylation reactions and the synthesis of amino acid derivatives such as aminoacyl adenylates and aminoacyl thioacids. We further demonstrate that carbon disulfide (CS2) also acts as an aqueous condensing agent via a mechanistic pathway similar to that involving COS. These experiments expand the scope of COS and CS2 in relation to prebiotic chemistry and suggest that peptide synthesis, the formation of diverse amino acid derivatives, and phosphorylation may have all shared a common chemical pathway, mediated by COS, on the prebiotic Earth.

 

Proteins, Peptides, Amino Acids, and Enzyme Inhibitors
8:00 AM-12:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006