185611-85-2Relevant articles and documents
Selective enzymatic removal of protecting groups: The phenylacetamide as amino protecting group in phosphopeptide synthesis
Waldmann, Herbert,Heuser, Axel,Schulze, Sonja
, p. 8725 - 8728 (1996)
The phenylacetamido (PhAc) amino protecting group can be removed from sensitive phosphopeptides by means of penicillin G acylase under mild conditions (pH 6.5, room temperature) and without attack on the peptide bonds, the C-terminal esters or the phosphates. In particular, under the conditions of the enzymatic reactions a β-elimination of the phosphate does not occur.
Selective enzymatic removal of protecting groups from phosphopeptides: Chemoenzymatic synthesis of a characteristic phosphopeptide fragment of the raf-1 kinase
Sebastian, Dagmar,Heuser, Axel,Schulze, Sonja,Waldmann, Herbert
, p. 1098 - 1108 (2007/10/03)
Base-labile biologically relevant phosphopeptides can advantageously be synthesized under very mild conditions and without undesired side reactions by employing the heptyl (Hep) ester as C-terminal or the phenylacetamide (PhAc) as N-terminal enzyme-labile protecting group. The lipase-mediated saponification of the heptyl ester blocking function was successfully applied in the construction of a characteristic selectively phosphorylated hydroxyamino acid fragment of Raf-1 kinase, an important member of the so-called Ras signal transduction pathway.
