c-di-GMP displays a monovalent metal ion-dependent polymorphism

J Am Chem Soc. 2004 Dec 29;126(51):16700-1. doi: 10.1021/ja0449832.


Cyclic diguanosine monophosphate (c-di-GMP) is known to be an important signaling molecule that regulates the formation of bacterial biofilms. We demonstrate here by UV, CD, and NMR that it displays a surprising polymorphism that varies with the monovalent counterion and is consistent with the formation of a G-quartet structure in K+ and a stacked structure in Li+ or Na+. The ability of this rigid molecule to adopt different alignments may be important to its biological role.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cations, Monovalent
  • Circular Dichroism
  • Cyclic GMP / analogs & derivatives*
  • Cyclic GMP / chemistry*
  • Metals, Alkali / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Spectrophotometry, Ultraviolet


  • Cations, Monovalent
  • Metals, Alkali
  • bis(3',5')-cyclic diguanylic acid
  • Cyclic GMP