Isostructural self-assembly of 2'-deoxyguanosine derivatives in aqueous and organic media

J Am Chem Soc. 2008 Aug 13;130(32):10492-3. doi: 10.1021/ja8039019. Epub 2008 Jul 22.


We report the self-assembly of a hydrophilic 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) derivative into a discrete and thermally stable hexadecameric supramolecule in aqueous media. We demonstrate that this hexadecamer is isostructural to the one formed by a related lipophilic derivative in organic media. This mAG moiety represents a rare example of a small-molecule recognition motif that is capable of assembling isostructurally and with high fidelity in both organic and aqueous media.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry*
  • Isomerism
  • Molecular Structure
  • Solvents / chemistry
  • Water / chemistry*


  • Solvents
  • Water
  • Deoxyguanosine