Clear Search sequence regions


  • 6 aminouracil (3)
  • catalysis (1)
  • electrons (1)
  • hydrogen (3)
  • hydrogen ion (1)
  • liquid (1)
  • sugar (1)
  • uracil (4)
  • Sizes of these terms reflect their relevance to your search.

    Following the suggestion that nucleoside analogues having their nucleobases joined to ribose via a carbon-carbon bond might easily arise prebiotically, the glycosylation of uracil carrying electron-donating substituents (Me, OH, OCH3, NH2) at its 5 or 6 positions was investigated. Of these, only 6-aminouracil gave glycosylated products in greater than 50% yield under simulated prebiotic conditions. The reaction provided four products, three of which were purified by preparative HPLC. The structure of the isolated compounds was determined by high-resolution mass spectrometry and NMR spectroscopy. The glycosylation products were, as expected, C-nucleosides, with the sugar having either a pyranose or a furanose structure, with the ratio depending on the precise conditions, implying reversible addition. Interestingly, the 6-aminouracil riboside displays two hydrogen bonding patterns, the "acceptor-donor-acceptor" pattern of uridine itself and (upon 180° rotation) the "acceptor-donor-donor" hydrogen bonding pattern. The second, in an artificially expanded genetic information system, is trivially called "V" and pairs with a purine analogue that presents the complementary "donor-acceptor-acceptor" hydrogen bonding pattern, trivially called "J.

    Citation

    Hyo-Joong Kim, Steven A Benner. Prebiotic glycosylation of uracil with electron-donating substituents. Astrobiology. 2015 Apr;15(4):301-6

    Expand section icon Mesh Tags

    Expand section icon Substances


    PMID: 25860300

    View Full Text