title: Phosphoramidate-peptide synthesis by solution- and solid-phase Staudinger-phosphite reactions.
abstract: The chemoselective incorporation of phosphoramidate moieties into peptides by a Staudinger-phosphite reaction of azides can be performed in many solvents, including water. In this report, we present two strategies for an efficient synthesis of phosphoramidate-containing peptides, in which the Staudinger-phosphite reaction is performed either on the solid support or in solution with aryl azido-containing peptides. The corresponding Staudinger reactions proceed in high conversion rates and deliver phosphoramidate peptides, in which the modification site is located in the middle of the peptide sequence.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Berlin, Germany.
authors.forename: Remigiusz A
authors.initials: RA
authors.lastname: Serwa
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Swiecicki
authors.forename: Denise
authors.initials: D
authors.lastname: Homann
authors.forename: Christian P R
authors.initials: CP
authors.lastname: Hackenberger
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000235:genetics; D017905:Phosphites / Q000737:chemistry*; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
chemical_list: D000577:Amides; D001386:Azides; D010455:Peptides; D017905:Phosphites; D010756:Phosphoric Acids; D012997:Solvents; C011067:phosphoramidic acid