Spatially addressed synthesis of amino- and amino-oxy-substituted 1, 3,5-triazine arrays on polymeric membranes

J Comb Chem. Jul-Aug 2000;2(4):361-9. doi: 10.1021/cc000012g.

Abstract

Effective spatially addressed parallel assembly of trisamino- and amino-oxy-1,3,5-triazines was achieved by applying the SPOT-synthesis technique on cellulose and polypropylene membranes. In addition to developing a suitable linker strategy and employing amines and phenolate ions as building blocks, a highly effective microwave-assisted nucleophilic substitution procedure at membrane-bound monochlorotriazines was developed. The 1,3, 5-triazines obtained could be cleaved in parallel from the solid support by TFA vapor to give compounds adsorbed on the membrane surface in a conserved spatially addressed format for analysis and screening. The reaction conditions developed were employed for the synthesis of 8000 cellulose-bound 1,3,5-triazines which were probed in parallel for binding to the anti-transforming growth factor-alpha monoclonal antibody Tab2 in order to identify epitope mimics.

MeSH terms

  • Amines*
  • Amino Acid Sequence
  • Antibodies, Monoclonal
  • Drug Design
  • Enzyme-Linked Immunosorbent Assay / methods
  • Epitopes / analysis
  • Membranes, Artificial
  • Molecular Sequence Data
  • Oxides
  • Peptides / chemistry
  • Polymers
  • Structure-Activity Relationship
  • Transforming Growth Factor alpha / chemistry
  • Transforming Growth Factor alpha / immunology*
  • Triazines / chemical synthesis*
  • Triazines / chemistry

Substances

  • Amines
  • Antibodies, Monoclonal
  • Epitopes
  • Membranes, Artificial
  • Oxides
  • Peptides
  • Polymers
  • Transforming Growth Factor alpha
  • Triazines