171775-77-2Relevant academic research and scientific papers
Preparation of phosphoamino acid derivatives with acid stable O-phosphono-protection for the Boc-mode solid-phase synthesis of phosphopeptides
Wakamiya,Saruta,Yasuoka,Kusumoto
, p. 2699 - 2703 (2007/10/03)
Boc-phosphoamino acid derivatives with O-[di(4-nitrobenzyl)- or dicyclohexylphosphono]-protection were prepared for application to the Boc-mode solid-phase synthesis of phosphopeptides. These protecting groups are both stable to TFA, but removable with a combination of trifluoromethanesulfonic acid and methylthiobenzene in TFA. Of these derivatives, N(α)-Boc-O-(dicyclohexylphosphono)serine and N(α)-Boc-O-(dicyclohexylphosphono)threonine were obtained as crystalline compounds to be favorably utilized as starting materials for solid-phase synthesis using an automated peptide synthesizer. On the other hand, N(α)-Boc-O-(dicyclohexylphosphono)tyrosine and all of the O-[di(4-nitrobenzyl)]phosphono derivatives were prepared as crystalline cyclohexylammonium or dicyclohexylammonium salts.
