Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)

Hua Zhang; Xuefei Li; Qiuyan Shi; Yu Li; Guiquan Xia; Long Chen; Zhigang Yang; Zhong-Xing Jiang

doi:10.1002/anie.201410309

Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)

Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3763-7. doi: 10.1002/anie.201410309. Epub 2015 Feb 4.

Authors

Hua Zhang¹, Xuefei Li, Qiuyan Shi, Yu Li, Guiquan Xia, Long Chen, Zhigang Yang, Zhong-Xing Jiang

Affiliation

¹ Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071 (China).

PMID: 25655646
DOI: 10.1002/anie.201410309

Abstract

A macrocyclic sulfate (MCS)-based approach to monodisperse poly(ethylene glycols) (M-PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62-membered macrocycle) as versatile precursors for a range of monofunctionalized M-PEGs. Through iterative nucleophilic ring-opening reactions of MCS without performing group protection and activation, a series of M-PEGs, including the unprecedented 64-mer (2850 Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M-PEGs.

Keywords: cyclization; macrocycles; macrocyclic sulfates; poly(ethylene glycol); synthetic methods.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Cyclization
Ethylene Glycols / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Polyethylene Glycols / chemical synthesis*
Polyethylene Glycols / chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

Ethylene Glycols
Polyethylene Glycols