title: Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation.
abstract: Small gold nanoparticles (AuNPs) that possess interfacial methyl-2-(diphenylphosphino)benzoate moieties have been successfully synthesized (Staudinger-AuNPs) and characterized by multi-nuclear MR spectroscopy, transmission electron microscopy (TEM), UV-Vis spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS). In particular, XPS was remarkably sensitive for characterization of the novel nanomaterial, and in furnishing proof of its interfacial reactivity. These Staudinger-AuNPs were found to be stable to the oxidation of the phosphine center. The reaction with benzyl azide in a Staudinger-Bertozzi ligation, as a model system, was investigated using (31)P NMR spectroscopy. This demonstrated that the interfacial reaction was clean and quantitative. To showcase the potential utility of these Staudinger-AuNPs in bioorganic chemistry, a AuNP bioconjugate was prepared by reacting the Staudinger-AuNPs with a novel azide-labeled CRGDK peptide. The CRGDK peptide could be covalently attached to the AuNP efficiently, chemoselectively, and with a high loading.
authors: The University of Western Ontario and the Centre for Materials and Biomaterials Research, Richmond Street, London, Ontario, Canada. mworkent@uwo.ca pgobbo2@uwo.ca.
authors: Pierangelo
authors: P
authors: Gobbo
authors: Wilson
authors: W
authors: Luo
authors: Sung Ju
authors: SJ
authors: Cho
authors: Xiaoxiao
authors: X
authors: Wang
authors: Mark C
authors: MC
authors: Biesinger
authors: Robert H E
authors: RH
authors: Hudson
authors: Mark S
authors: MS
authors: Workentin
mesh_terms: D001386:Azides / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008745:Methylation; D053758:Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure; D009842:Oligopeptides / Q000737:chemistry; D010316:Particle Size; D010720:Phosphines / Q000737:chemistry*; D056951:Photoelectron Spectroscopy; D013818:Thermogravimetry
chemical_list: D001386:Azides; D001565:Benzoates; D009842:Oligopeptides; D010720:Phosphines; D006046:Gold