Metal-modified nucleobase pairs and triplets as cytosine receptors

Chemistry. 2001 May 18;7(10):2104-13. doi: 10.1002/1521-3765(20010518)7:10<2104::aid-chem2104>3.0.co;2-f.

Abstract

A preorganized cationic receptor 2 for cytosine (C) is described which is composed of trans-a2PtII (a= NH3 or CH3NH2) cross-linked modules with adenine (A), guanine (G), and uracil (U) or thymine (T) model nucleobases. The functions of these three modules are as follows: i) Adenine orientates the two other bases at right angles, thus producing the L-shape of the receptor. ii) Guanine is the primary receptor. iii) Uracil or thymine act as coreceptors. Compared with the normal Watson-Crick pair between G and C, the association constant between 2 and C increases by a factor of 3 (in DMSO). As deduced from 1H NMR spectroscopy and confirmed by the X-ray crystal structure of the C adduct 4b, cytosine is fixed through five hydrogen bonds to the receptor, one of which involves the aromatic H(5) of C. A comparison of C binding is made with a structurally related linkage isomer receptor as well as the precursor molecule trans[alpha2PtAG]2+. The potential of modular, cationic receptors is illustrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pairing*
  • Cations
  • Crystallography, X-Ray
  • Cytosine / chemistry
  • Cytosine / metabolism*
  • Ligands
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Platinum / chemistry*
  • Purines / chemistry
  • Pyrimidines / chemistry
  • Receptors, Drug / chemistry
  • Receptors, Drug / metabolism*

Substances

  • Cations
  • Ligands
  • Purines
  • Pyrimidines
  • Receptors, Drug
  • Platinum
  • Cytosine