DEUSS: a perdeuterated poly(oxyethylene)-based resin for improving HRMAS NMR studies of solid-supported molecules.
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.
Poschalko
Alexander
A
Vienna University of Technology, Institute of Applied Synthetic Chemistry, 1060 Vienna, Austria.
Lancelot
Nathalie
N
Marin
Julien
J
Larras
Virginie
V
Limal
David
D
Elbayed
Karim
K
Raya
Jesus
J
Piotto
Martial
M
Briand
Jean-Paul
JP
Guichard
Gilles
G
Bianco
Alberto
A
D000837:Anion Exchange Resins / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D011092:Polyethylene Glycols / Q000737:chemistry*
D000837:Anion Exchange Resins; D011092:Polyethylene Glycols