Issue 13, 2016

Chromatography-free synthesis of monodisperse oligo(ethylene glycol) mono-p-toluenesulfonates and quantitative analysis of oligomer purity

Abstract

Poly(ethylene glycol) (PEG) is a common building block for complex functional molecules. Because of its chain flexibility and hydrophilicity, it is widely used in bioconjugation chemistry. Modern applications require PEGs of high purity, hence well-defined, monodisperse PEG oligomers are gaining more attention. Here we report a large-scale synthetic procedure for monodisperse oligo(ethylene glycol) mono-p-toluenesulfonates, convenient intermediates of various heterobifunctional PEG derivatives. This method features no chromatographic purification, low total material cost and high purity of the products. In addition, oligomer dispersity of the products is determined quantitatively using reverse-phase HPLC and a number of bioconjugation-related functionalized PEG derivatives are prepared from the synthesized toluenesulfonates.

Graphical abstract: Chromatography-free synthesis of monodisperse oligo(ethylene glycol) mono-p-toluenesulfonates and quantitative analysis of oligomer purity

Supplementary files

Article information

Article type
Paper
Submitted
22 Jan 2016
Accepted
26 Feb 2016
First published
29 Feb 2016
This article is Open Access
Creative Commons BY-NC license

Polym. Chem., 2016,7, 2389-2394

Chromatography-free synthesis of monodisperse oligo(ethylene glycol) mono-p-toluenesulfonates and quantitative analysis of oligomer purity

A. M. Wawro, T. Muraoka and K. Kinbara, Polym. Chem., 2016, 7, 2389 DOI: 10.1039/C6PY00127K

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