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Synthetic Organic Chemistry

5. Bioorthogonal transformations

5. Bioorthogonal transformations

In close collaboration with the group De Koster/Back/De Jong (SILS, UvA) selective organic reactions are developed in order to sequester specific peptides in complex biological mixtures.

Especially work by the groups of Schultz and Tirrell enabled the incorporation of noncoded amino acids into proteins using the natural biomachinery. Work is in progress to prepare water compatible resins with groups able to sequester, by click chemistry or Staudinger ligations, azide-containing proteins.

Recently, it was serendipitously found that azidohomoalanine-containing proteins are cleaved C-terminally to this residue by phosphine addition. In a recently granted ECHO project we will further develop this cleavage reaction as a novel tool to purify and characterize proteins.