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In order to elucidate the role of protein tyrosine phosphorylation involved in various intracellular signaling pathways, peptides containing O-phosphotyrosine have been developed. However, in order to improve the stability of the phosphorylated amino acid, we have designed some years ago a hydrolytically stable analogue, the 4-(phosphonomethyl)phenylalanine (Pmp). Introduced in peptide sequences,...
A new synthesis of N-Fmoc 4-phosphonomethyl-D,L-phenylalanine protected under di-tert-butyl or dimethyl phosphonate forms (Fmoc-Pmp(OR) 2 ), suitable for solid phase peptide synthesis is described. Resolution of these hydrolytically stable analogs of O-phosphotyrosine was tried either by fractional recrystallization of diastereoisomeric salts or by using the subtilisin Carlsberg esterase...
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