title: Chemoselective bioconjugation of triazole phosphonites in aqueous media.
abstract: Readily accessible and versatile phosphonite building blocks with improved stability against hydrolysis were used for the efficient metal-free functionalization of peptides and proteins in aqueous buffers at low micromolar concentrations. The application of this protocol to the immobilization of a Rasa1-SH2 domain revealed high binding affinity to the human T-cell protein ADAP and supports the applicability of triazole phosphonites for protein modifications without harming their function.
authors.affiliation: Leibniz-Institut für Molekulare Pharmakologie (FMP), Robert-Roessle-Str. 10, 13125 Berlin (Germany).
authors.forename: M Robert J
authors.initials: MR
authors.lastname: Vallée
authors.forename: Paul
authors.initials: P
authors.lastname: Majkut
authors.forename: Dagmar
authors.initials: D
authors.lastname: Krause
authors.forename: Michael
authors.initials: M
authors.lastname: Gerrits
authors.forename: Christian P R
authors.initials: CP
authors.lastname: Hackenberger
mesh_terms: D048868:Adaptor Proteins, Signal Transducing / Q000737:chemistry / Q000378:metabolism; D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006801:Humans; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D010757:Phosphorous Acids / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D020729:p120 GTPase Activating Protein / Q000737:chemistry / Q000378:metabolism; D018909:src Homology Domains
chemical_list: D048868:Adaptor Proteins, Signal Transducing; D000480:Alkynes; D001386:Azides; D010455:Peptides; D010757:Phosphorous Acids; C557248:RASA1 protein, human; D014230:Triazoles; D020729:p120 GTPase Activating Protein; D014867:Water; D003300:Copper
keywords: Staudinger reaction; bioorthogonal; chemoselectivity; phosphonites; protein conjugation