Get access

Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides Tagged with 2,4-Disubstituted 5-Aminopyrimidines as Recognition Elements

Authors

  • Gopi Kumar Mittapalli Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    Search for more papers by this author
  • Yazmin M. Osornio Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    Search for more papers by this author
  • Miguel A. Guerrero Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    Search for more papers by this author
  • Kondreddi Ravinder Reddy Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    Search for more papers by this author
  • Ramanarayanan Krishnamurthy Prof. Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    Search for more papers by this author
  • Albert Eschenmoser Prof. Dr.

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-9573
    2. Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, HCI Hönggerberg, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1043
    Search for more papers by this author

  • Chemistry of α-Aminonitriles, Part 46. For Part 45, see the preceding paper (reference 1). This work was supported by the Skaggs Research Foundation. G.K.M., Y.M.O, M.A.G, and K.R.R. are Skaggs Postdoctoral Fellows.

Abstract

original image

Bit different: 2,4-Dioxo- and 2,4-diamino-5-aminopyrimidine nuclei attached to an oligodipeptide backbone display a disparity in their base-pairing strength which is opposite to that shown by corresponding triazines. This behavior points to a remarkable correlation between pairing strength and ΔpKa values of pairs of complementary bases.

Ancillary