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      N-Carboxyanhydride-Mediated Fatty Acylation of Amino Acids and Peptides for Functionalization of Protocell Membranes

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          Abstract

          Early protocells are likely to have arisen from the self-assembly of RNA, peptide, and lipid molecules that were generated and concentrated within geologically favorable environments on the early Earth. The reactivity of these components in a prebiotic environment that supplied sources of chemical energy could have produced additional species with properties favorable to the emergence of protocells. The geochemically plausible activation of amino acids by carbonyl sulfide has been shown to generate short peptides via the formation of cyclic amino acid N-carboxyanhydrides (NCAs). Here, we show that the polymerization of valine-NCA in the presence of fatty acids yields acylated amino acids and peptides via a mixed anhydride intermediate. Notably, N α-oleoylarginine, a product of the reaction between arginine and oleic acid in the presence of valine-NCA, partitions spontaneously into vesicle membranes and mediates the association of RNA with the vesicles. Our results suggest a potential mechanism by which activated amino acids could diversify the chemical functionality of fatty acid membranes and colocalize RNA with vesicles during the formation of early protocells.

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          Author and article information

          Journal
          J Am Chem Soc
          J Am Chem Soc
          ja
          jacsat
          Journal of the American Chemical Society
          American Chemical Society
          0002-7863
          1520-5126
          28 November 2016
          28 December 2016
          : 138
          : 51
          : 16669-16676
          Affiliations
          []Howard Hughes Medical Institute, Department of Molecular Biology and Center for Computational and Integrative Biology, Massachusetts General Hospital , 185 Cambridge Street, Boston, Massachusetts 02114, United States
          []Department of Genetics, Harvard Medical School , 77 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States
          [§ ]Department of Biosciences, Åbo Akademi University , Åbo FI-20520, Finland
          []Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States
          Author notes
          Article
          10.1021/jacs.6b08801
          7547885
          27959544
          13e5f24a-7064-475e-827d-e019b2a6f44b

          This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

          History
          : 22 August 2016
          Categories
          Article
          Custom metadata
          ja6b08801
          ja6b08801

          Chemistry
          Chemistry

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