737761-24-9Relevant academic research and scientific papers
Gel-phase 19F NMR spectral quality for resins commonly used in solid-phase organic synthesis; a study of peptide solid-phase glycosylations
Mogemark, Mickael,Gardmo, Frida,Tengel, Tobias,Kihlberg, Jan,Elofsson, Mikael
, p. 1770 - 1776 (2004)
The spectroscopic properties for seven different commercial resins used in solid-phase synthesis were investigated with F NMR spectroscopy. A fluorine-labeled dipeptide was synthesized on each resin, and the resolution of the 19F resonances in CDCl3. DMSO-d6, benzene-d6 and CD3OD were measured with a conventional NMR spectrometer, i.e. without using magic angle spinning. In general, resins containing polyethylene glycol) chains (ArgoGel, TentaGel and PEGA) were found to be favorable for the 19F NMR spectral quality. Three serine containing tri-, penta-. and heptapeptides were then prepared on an ArgoGel resin functionalized with a fluorine-labeled linker. The resin bound peptides were glycosylated utilizing a thiogalactoside glycosyl donor carrying fluorine-labeled protective groups. Monitoring of the glycosylations with gel-phase 19F NMR spectroscopy allowed each glycopeptide to be formed in ～80% yield, using a minimal amount of glycosyl donor (3 × 2 equivalents). In addition, it was found that the glycosylation yields were independent of peptide length.
