Natural peptides as building blocks for the synthesis of large protein-like molecules with hydrazone and oxime linkages.
K Rose, W Zeng, PO Regamey, IV Chernushevich, KG Standing, HF Gaertner
Bioconjugate Chemistry | Published : 1996
Methods are known for the production of synthetic protein-like molecules of nonlinear architecture with molecular masses in the 10-20 kDa range. To synthesize such compounds of higher molecular mass and complexity, chemoselective ligation of natural (as opposed to synthetic) peptide building blocks was studied. In preliminary experiments with model peptides, conditions for the formation of peptide oximes were investigated, and their stability at alkaline pH was examined, to resolve a literature controversy. It was found that low pH (down to 2.1) was suitable for polyoxime formation and that the oxime bond was stable for up to 65 h at pH 8 and for more than 2 h at pH 9. Then, using natural pe..View full abstract