Synthesis, characterization and structures of methylmercury complexes with selenoamino acids

Dalton Trans. 2009 Aug 7:(29):5766-72. doi: 10.1039/b903863a. Epub 2009 Jun 10.

Abstract

Four new methylmercury-selenoamino acid complexes were synthesized, including methylmercury-L-selenoglutathionate, methylmercury-D,L-selenopenicillaminate, and two methylmercury-L-selenomethioninate complexes (one via a Hg-Se bonding and the other Hg-N bonding). All the complexes were characterized by NMR ((1)H, (13)C, (77)Se and (199)Hg), FT-IR and mass spectra. Their molecular structures were established by single crystal X-ray crystallography (for the Hg-N bonding methylmercury-L-selenomethioninate) and by quantum mechanical calculations using Gaussian-03 with the hybrid functional B3LYP/SDD. All four complexes were found to chemically and structurally resemble their sulfur analogues, with a slightly stronger binding affinity of Hg to Se than to S, suggesting chemical and structural mimicry might play a role in methylmercury-selenium antagonism in biological systems.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Crystallography, X-Ray
  • Methylmercury Compounds / chemical synthesis*
  • Methylmercury Compounds / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Selenium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Methylmercury Compounds
  • Selenium Compounds