Get access

Amphiphilic DNA Duplex Stabilized by a Hydrophobic Zipper

Authors

  • Chikara Dohno,

    1. Department of Regulatory Bioorganic Chemistry, The Institute of Scientific and Industrial Research (ISIR), Osaka University, Ibaraki 567-0047, Japan, Fax: +81-6-6879-8459
    2. PRESTO, Japan Science and Technology Agency, 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan Homepage: http://www.emergence.jst.go.jp/
    Search for more papers by this author
  • Tomonori Shibata,

    1. Department of Regulatory Bioorganic Chemistry, The Institute of Scientific and Industrial Research (ISIR), Osaka University, Ibaraki 567-0047, Japan, Fax: +81-6-6879-8459
    Search for more papers by this author
  • Masatsugu Okazaki,

    1. Department of Regulatory Bioorganic Chemistry, The Institute of Scientific and Industrial Research (ISIR), Osaka University, Ibaraki 567-0047, Japan, Fax: +81-6-6879-8459
    Search for more papers by this author
  • Shingo Makishi,

    1. Department of Regulatory Bioorganic Chemistry, The Institute of Scientific and Industrial Research (ISIR), Osaka University, Ibaraki 567-0047, Japan, Fax: +81-6-6879-8459
    Search for more papers by this author
  • Kazuhiko Nakatani

    1. Department of Regulatory Bioorganic Chemistry, The Institute of Scientific and Industrial Research (ISIR), Osaka University, Ibaraki 567-0047, Japan, Fax: +81-6-6879-8459
    Search for more papers by this author

Abstract

We have synthesized a new amphiphilic DNA containing an internal hydrophobic region consisting of dodecyl phosphotriester linkages (dod-DNA). dod-DNAs of any arbitrary sequence can be synthesized by standard automated solid-phase synthesis using a set of nucleoside dodecyl phosphoramidites. Although replacement of a phosphodiester linkage with the hydrophobic phosphotriester linkage tended to decrease the thermodynamic stability of the duplex, when multiple dodecyl groups were introduced into both strands of a DNA duplex in a face-to-face arrangement, the resulting duplex was strongly stabilized by the interstrand hydrophobic interaction. The hydrophobic zipper formation provides a tightly associated, electroneutral, and highly hydrophobic region in the originally hydrophilic DNA duplex. As the hydrophobic properties can be adjusted by varying the encoded sequence, dod-DNA is an easy-to-design amphiphilic molecule for controllable vesicles and membrane biotechnology.

Ancillary