DEUSS: a perdeuterated poly(oxyethylene)-based resin for improving HRMAS NMR studies of solid-supported molecules |
| |
Authors: | Poschalko Alexander Lancelot Nathalie Marin Julien Larras Virginie Limal David Elbayed Karim Raya Jesus Piotto Martial Briand Jean-Paul Guichard Gilles Bianco Alberto |
| |
Institution: | Vienna University of Technology, Institute of Applied Synthetic Chemistry, 1060 Vienna, Austria. |
| |
Abstract: | A novel resin called DEUSS (perdeuterated poly(oxyethylene)-based solid support) has been prepared by anionic polymerization of deuterated D4]ethylene oxide, followed by cross-linking with deuterated epichlorohydrin. 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 corresponding nondeuterated poly(oxyethylene)poly(oxypropylene) (POEPOP) resin, thus facilitating detailed HRMAS NMR studies of covalently linked molecules. This 1H 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 spectroscopy. 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. |
| |
Keywords: | combinatorial chemistry NMR spectroscopy oligoureas peptides poly(oxyethylene) resins |
本文献已被 PubMed 等数据库收录! |
|