Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation

Organic & Biomolecular Chemistry
Pierangelo GobboMark S Workentin

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.

References

Mar 17, 2000·Science·E Saxon, C R Bertozzi
Sep 25, 2003·Journal of the American Chemical Society·Matthew B SoellnerRonald T Raines
Feb 24, 2005·Journal of the American Chemical Society·Fiona L LinCarolyn R Bertozzi
Jan 28, 2006·Angewandte Chemie·Anja WatzkeHerbert Waldmann
Dec 19, 2006·ACS Chemical Biology·Nicholas J AgardCarolyn R Bertozzi
Aug 21, 2008·Accounts of Chemical Research·Catherine J MurphySarah C Baxter
Dec 17, 2009·Journal of Controlled Release : Official Journal of the Controlled Release Society·Dakrong PissuwanMichael B Cortie
Jan 19, 2010·Proceedings of the National Academy of Sciences of the United States of America·Pamela V ChangCarolyn R Bertozzi
Sep 14, 2010·Chembiochem : a European Journal of Chemical Biology·Kimberly E BeattyDavid A Tirrell
Jun 21, 2011·Chemical Society Reviews·Christine I SchillingStefan Bräse
Sep 3, 2011·Angewandte Chemie·Sander S van BerkelJan C M van Hest
Nov 17, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Kurtis D HartlenMark S Workentin
Jun 15, 2012·Bioconjugate Chemistry·Shige H YoshimuraKunio Takeyasu
Aug 14, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Pierangelo Gobbo, Mark S Workentin
Jan 31, 2013·Molecular Pharmaceutics·Aneta J MieszawskaDavid P Cormode
Apr 4, 2013·Chemical Communications : Chem Comm·Pierangelo GobboMark S Workentin
May 1, 2013·Organic & Biomolecular Chemistry·Mariya ChigrinovaJohn Paul Pezacki
May 7, 2013·Journal of the American Chemical Society·Jie HeZhihong Nie
Jun 19, 2013·Current Opinion in Chemical Biology·Dina GrohmannPhilip Tinnefeld
Jan 23, 2014·Chemical Society Reviews·B E I RamakersD W P M Löwik
Feb 1, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Julio C AzcárateMariano H Fonticelli
Apr 18, 2014·Bioconjugate Chemistry·Mathias King, Alain Wagner
Sep 18, 2014·ACS Nano·Hee-Young LeeKyle J M Bishop
Apr 7, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Pierangelo GobboMark S Workentin

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Citations

Jan 24, 2021·Analytical and Bioanalytical Chemistry·Ying LuoSuri S Iyer
Jun 9, 2021·Chemical Reviews·Tyler K HeissJennifer A Prescher
May 2, 2020·Chemical Reviews·Christin BednarekStefan Bräse

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