Molecular recognition motifs in cytidinium and 2'-deoxycytidinium salts with composite anions

Acta Biochim Pol. 1998;45(4):917-28.

Abstract

In the crystal structures of N3-protonated cytidinium and 2'-deoxycytidinium salts with composite XYn anions capable of accepting hydrogen bonds through their Y atoms, the dominating motif of cytosinium...anion interactions consists of a pair of hydrogen bonds donated from the N3+ -H protonation site and from the exoamino N4-H41 group cis to N3, and accepted by two Y centers of one anion. This multipoint recognition pattern is stable and robust and thus can be classified as a supramolecular synthon. In a broader group of N3-protonated, N1-substituted cytosinium salts with composite anions it occurs with 70% frequency. The C5 side of the cytosine ring mimics the N3+ -H type synthon and shows a propensity to form an analogous motif in which a C5-H5...Y hydrogen bond replaces the strong N3+ -H...Y interaction. Since the C-H...Y bond is much weaker, the secondary motif shows higher deformability and is less frequent (44%).

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Anions / chemistry*
  • Cations / chemistry*
  • Crystallography
  • Cytidine / chemistry*
  • Deoxycytidine / chemistry*
  • Deoxycytosine Nucleotides / chemistry
  • Hydrogen Bonding
  • Models, Molecular

Substances

  • Anions
  • Cations
  • Deoxycytosine Nucleotides
  • Deoxycytidine
  • Cytidine