A DNA-Templated Aldol Reaction as a Model for the Formation of Pentose Sugars in the RNA World

Authors

  • Michael Oberhuber Dr.,

    1. Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2943
    2. Current address: Institute of Organic Chemistry and Center for Molecular Biosciences, Leopold-Franzens University of Innsbruck, 6020 Innsbruck, Austria
    Search for more papers by this author
  • Gerald F. Joyce Prof. Dr.

    1. Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2943
    Search for more papers by this author

  • This work was supported by NASA and The Skaggs Institute for Chemical Biology at The Scripps Research Institute. M.O. was supported by postdoctoral fellowship J2296 from the Austrian National Science Fund (FWF) and the Max Kade Foundation.

Abstract

original image

Sugar on a stick: A DNA template can bind two complementary oligonucleotides, one derivatized with glyceraldehyde (blue) and the other with glycolaldehyde (red), resulting in a cross-aldol reaction that forms pentose sugars. This reaction system serves as a model for the RNA-catalyzed synthesis of ribose, which is relevant to a presumed RNA-based metabolism during the early history of life on Earth.

Ancillary