Covalently bonded platinum(II) complexes of alpha-amino acids and peptides as a potential tool for protein labeling

Chemistry. 2002 Dec 2;8(23):5368-76. doi: 10.1002/1521-3765(20021202)8:23<5368::AID-CHEM5368>3.0.CO;2-D.

Abstract

Arylplatinum(II) complexes have been covalently bonded to the N and C termini and to the alpha-carbon of various amino acid derivatives. These organometallic-functionalized amino acid compounds can be converted into the corresponding free amino acids under both basic and acidic conditions; this demonstrates the excellent stability properties of these biomolecules. Due to the NMR activity displayed by the 195Pt nucleus (natural abundance 33.8%, I = 1/2) these compounds are functional bio-markers. Furthermore, the ability of the arylplatinum functional group to bind SO2 gas, selectively and reversibly as indicated by changes in the spectroscopic properties (1H, 13C, 195Pt NMR and UV spectra) of these compounds, allows for the potential use of these complexes as in vitro biosensors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Biomarkers
  • Biosensing Techniques
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy / methods
  • Organoplatinum Compounds / chemistry*
  • Organoplatinum Compounds / metabolism
  • Peptides / chemistry*
  • Peptides / metabolism
  • Sulfur Dioxide / chemistry
  • Sulfur Dioxide / metabolism

Substances

  • Amino Acids
  • Biomarkers
  • Indicators and Reagents
  • Organoplatinum Compounds
  • Peptides
  • Sulfur Dioxide