Design of maleimide-functionalised electrodes for covalent attachment of proteins through free surface cysteine groups

Chemistry. 2014 May 5;20(19):5550-4. doi: 10.1002/chem.201400246. Epub 2014 Apr 10.

Abstract

Mixed two-component monolayers on glassy carbon are prepared by electrochemical oxidation of N-(2-aminoethyl)acetamide and mono-N-Boc-hexamethylenediamine in mixed solution. Subsequent N-deprotection, amide coupling and solid-phase synthetic steps lead to electrode-surface functionalisation with maleimide, with controlled partial coverage of this cysteine-binding group at appropriate dilution for covalent immobilisation of a model redox-active protein, cytochrome c, with high coverage (≈7.5 pmol cm(-2) ).

Keywords: cyclic voltammetry; electrochemistry; proteins; solid-phase synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemistry
  • Biosensing Techniques
  • Cysteine / chemistry*
  • Cytochromes c / chemistry*
  • Diamines / chemistry*
  • Electrochemistry
  • Electrodes
  • Maleimides / chemical synthesis*
  • Maleimides / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Proteins / chemistry*
  • Surface Properties

Substances

  • Acetamides
  • Diamines
  • Maleimides
  • Proteins
  • mono-N-Boc-hexamethylenediamine
  • Cytochromes c
  • N-(2-aminoethyl)acetamide
  • Cysteine