Solid phase synthesis of peptides containing a phosphoserine - sulfur mustard adduct

Solid phase synthesis of peptides containing a serine thiodiglycol phosphate residue has been achieved by following a global on-resin phosphorylation strategy with a functionalized benzyl phosphoramidite. To preclude cleavage of the acid labile thiodiglycol phosphate ester during deprotection, the thioether functionality was temporarily protected as a sulfoxide.

Synthesis of peptides containing serine thiodiglycol phosphate (1) has been achieved by following a global on-resin phosphorylation strategy with the functionalized benzyl phosphoramidite 2.Figure optionsDownload full-size imageDownload as PowerPoint slide