Phosphoramidate-peptide synthesis by solution- and solid-phase Staudinger-phosphite reactions.
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.
Serwa
Remigiusz A
RA
Institut für Chemie und Biochemie, Freie Universität Berlin, Berlin, Germany.
Swiecicki
Jean-Marie
JM
Homann
Denise
D
Hackenberger
Christian P R
CP
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
D000577:Amides; D001386:Azides; D010455:Peptides; D017905:Phosphites; D010756:Phosphoric Acids; D012997:Solvents; C011067:phosphoramidic acid