DEUSS:A Perdeuterated Poly(oxyethylene)-Based Resin for Improving HRMAS NMR Studies of Solid-Supported Molecules

摘要

A novel resin called DEUSS (perdeuterated poly(oxyethylene)-based solid support) has been prepared by anionic polymerization of deuterat-ed [D_4]ethylene oxide,followed by cross-linking with deuterated epichloro-hydrin.DEUSS can be suspended in a wide range of solvents including organic and aqueous solutions,in which it displays a high swelling capacity.As measured by proton HRMAS of the swollen polymer,the signal intensity of the oxyethylene protons is reduced by a factor of 110 relative to the corre-sponding nondeuterated poly(oxyeth-ylene)poly(oxypropylene) (POEPOP) resin,thus facilitating detailed HRMAS NMR studies of covalently linked molecules.This 'H NMR invisible matrix was used for the solid-phase synthesis of peptides,oligoureas,and a series of amides as well as their characterization by HRMAS NMR spectros-copy.On-bead NMR spectra of high quality and with resolution comparable to that of liquid samples were obtained and readily interpreted.The complete absence of the parasite resin signals will be of great advantage,for example,for the optimization of multistep solid-phase stereoselective reactions,and for the conformational study of resin-bound molecules in a large variety of solvents.