title: Staudinger-phosphonite reactions for the chemoselective transformation of azido-containing peptides and proteins.
abstract: Site-specific functionalization of proteins by bioorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with oligoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
authors.forename: M Robert J
authors.initials: MR
authors.lastname: Vallée
authors.forename: Paul
authors.initials: P
authors.lastname: Majkut
authors.forename: Ina
authors.initials: I
authors.lastname: Wilkening
authors.forename: Christoph
authors.initials: C
authors.lastname: Weise
authors.forename: Gregor
authors.initials: G
authors.lastname: Müller
authors.forename: Christian P R
authors.initials: CP
authors.lastname: Hackenberger
mesh_terms: D001386:Azides / Q000737:chemistry*; D002147:Calmodulin / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry*; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D001386:Azides; D002147:Calmodulin; D009943:Organophosphorus Compounds; D010455:Peptides; D011506:Proteins; D014867:Water