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DEUSS: A Perdeuterated Poly(oxyethylene)‐Based Resin for Improving HRMAS NMR Studies of Solid‐Supported Molecules
Author(s) -
Poschalko Alexander,
Lancelot Nathalie,
Marin Julien,
Larras Virginie,
Limal David,
Elbayed Karim,
Raya Jesus,
Piotto Martial,
Briand JeanPaul,
Guichard Gilles,
Bianco Alberto
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400373
Subject(s) - epichlorohydrin , chemistry , molecule , polymer chemistry , polymer , deuterium , nuclear magnetic resonance spectroscopy , polymerization , organic chemistry , quantum mechanics , physics
A novel resin called DEUSS (per deu terated poly(oxyethylene)‐based s olid s upport) has been prepared by anionic polymerization of deuterated [D 4 ]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 1 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 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.