Biomimetic seleninates and selenonates

J Am Chem Soc. 2008 Jul 23;130(29):9234-5. doi: 10.1021/ja8034448. Epub 2008 Jun 25.

Abstract

The synthesis of a variety of pyranose-, nucleoside-, (amino acid)-, and polyhydric-based seleninic and selenonic acids by DMDO oxidation of the corresponding selenoesters is reported, as well as some unusual coupling reactions of the seleninate and selenonate functionality with biological nucleophilic groups (sulfhydryl, indole, phenol, imidazole, carboxamide) that are found in proteins and enzyme active sites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amino Acids / chemical synthesis
  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / chemistry
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / chemistry
  • Imidazoles / chemistry
  • Indoles / chemistry
  • Nucleosides / chemical synthesis
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Oxidation-Reduction
  • Phenols / chemistry
  • Pyrans / chemical synthesis
  • Sulfhydryl Compounds / chemistry

Substances

  • Amides
  • Amino Acids
  • Carboxylic Acids
  • Imidazoles
  • Indoles
  • Nucleosides
  • Organoselenium Compounds
  • Phenols
  • Pyrans
  • Sulfhydryl Compounds
  • seleninic acid