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Issue 15, 2015
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Small gold nanoparticles for interfacial Staudinger–Bertozzi ligation

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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 31P 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.

Graphical abstract: Small gold nanoparticles for interfacial Staudinger–Bertozzi ligation

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Supplementary files

Article information

24 Feb 2015
11 Mar 2015
First published
11 Mar 2015

Org. Biomol. Chem., 2015,13, 4605-4612
Article type
Author version available

Small gold nanoparticles for interfacial Staudinger–Bertozzi ligation

P. Gobbo, W. Luo, S. J. Cho, X. Wang, M. C. Biesinger, R. H. E. Hudson and M. S. Workentin, Org. Biomol. Chem., 2015, 13, 4605
DOI: 10.1039/C5OB00372E

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