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Gel-phase F-19 NMR spectral quality for resins commonly used in solid-phase organic synthesis: a study of peptide solid-phase glycosylations
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2004 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 2, 1770-1776 p.Article in journal (Refereed) Published
Abstract [en]

The spectroscopic properties for seven different commercial resins used in solid-phase synthesis were investigated with F-19 NMR spectroscopy. A fluorine-labeled dipeptide was synthesized on each resin, and the resolution of the F-19 resonances in CDCl3, DMSO-d(6), benzene-d(6) and CD3OD were measured with a conventional NMR spectrometer, i.e. without using magic angle spinning. In general, resins containing poly(ethylene glycol) chains (ArgoGel, TentaGel and PEGA) were found to be favorable for the F-19 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 F-19 NMR spectroscopy allowed each glycopeptide to be formed in similar to80% yield, using a minimal amount of glycosyl donor (3 x 2 equivalents). In addition, it was found that the glycosylation yields were independent of peptide length.

Place, publisher, year, edition, pages
2004. Vol. 2, 1770-1776 p.
Identifiers
URN: urn:nbn:se:umu:diva-14079DOI: 10.1039/b404802dOAI: oai:DiVA.org:umu-14079DiVA: diva2:153750
Available from: 2007-05-22 Created: 2007-05-22 Last updated: 2011-03-31Bibliographically approved
In thesis
1. Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
Open this publication in new window or tab >>Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

An efficient and versatile non-destructive method to analyze the progress of solid-phase glycoconjugate synthesis with gel-phase 19F NMR spectroscopy is described. The method relies on use of fluorinated linkers and building blocks carrying fluorinated protective groups. Commercially available fluorinated reagents have been utilized to attach the protective groups.

The influence of resin structures for seven commercial resins upon resolution of gel-phase 19F NMR spectra was investigated. Two different linkers for oligosaccharide synthesis were also developed and successfully employed in preparation of α-Gal trisaccharides and a n-pentenyl glycoside. Finally, reaction conditions for solid-phase peptide glycosylations were established.

Place, publisher, year, edition, pages
Umeå: Kemi, 2005. 82 p.
Keyword
Organic chemistry, Solid-phase synthesis, protective groups, linkers, monitoring, gel-phase, 19F NMR spectroscopy, carbohydrates, oligosaccharides, glycopeptides, Organisk kemi
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-438 (URN)91-7305-792-4 (ISBN)
Public defence
2005-01-21, 13:00
Available from: 2005-01-28 Created: 2005-01-28 Last updated: 2012-06-29Bibliographically approved

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Tengel, TobiasKihlberg, JanElofsson, Mikael

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