A Highly Efficient Single-Chain Metal-Organic Nanoparticle Catalyst for Alkyne-Azide "click" Reactions in Water and in Cells

Yugang Bai, Xinxin Feng, Hang Xing, Yanhua Xu, Boo Kyung Kim, Noman Baig, Tianhui Zhou, Andrew A. Gewirth, Yi Lu, Eric Oldfield, Steven C. Zimmerman

Research output: Contribution to journalArticle

Abstract

We show that copper-containing metal-organic nanoparticles (MONPs) are readily synthesized via Cu(II)-mediated intramolecular cross-linking of aspartate-containing polyolefins in water. In situ reduction with sodium ascorbate yields Cu(I)-containing MONPs that serve as highly efficient supramolecular catalysts for alkyne-azide "click chemistry" reactions, yielding the desired 1,4-adducts at low parts per million catalyst levels. The nanoparticles have low toxicity and low metal loadings, making them convenient, green catalysts for alkyne-azide "click" reactions in water. The Cu-MONPs enter cells and perform efficient, biocompatible click chemistry, thus acting as intracellular nanoscale molecular synthesizers.

Original languageEnglish (US)
Pages (from-to)11077-11080
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number35
DOIs
StatePublished - Sep 7 2016

    Fingerprint

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this