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Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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 [en]
Organic chemistry, Solid-phase synthesis, protective groups, linkers, monitoring, gel-phase, 19F NMR spectroscopy, carbohydrates, oligosaccharides, glycopeptides
Keyword [sv]
Organisk kemi
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-438ISBN: 91-7305-792-4 (print)OAI: oai:DiVA.org:umu-438DiVA: diva2:143454
Public defence
2005-01-21, 13:00
Available from: 2005-01-28 Created: 2005-01-28 Last updated: 2012-06-29Bibliographically approved
List of papers
1. Gel-phase F-19 NMR spectral quality for resins commonly used in solid-phase organic synthesis: a study of peptide solid-phase glycosylations
Open this publication in new window or tab >>Gel-phase F-19 NMR spectral quality for resins commonly used in solid-phase organic synthesis: a study of peptide solid-phase glycosylations
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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.

Identifiers
urn:nbn:se:umu:diva-14079 (URN)10.1039/b404802d (DOI)
Available from: 2007-05-22 Created: 2007-05-22 Last updated: 2017-12-14Bibliographically approved
2. Monitoring Solid-Phase Glycoside Synthesis with 19F NMR Spectroscopy
Open this publication in new window or tab >>Monitoring Solid-Phase Glycoside Synthesis with 19F NMR Spectroscopy
2001 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 3, no 10, 1463-1466 p.Article in journal (Refereed) Published
Abstract [en]

A simple and efficient method for monitoring and optimizing carbohydrate synthesis on polymeric support by using 19F NMR spectroscopy is described. The method relies on the use of fluorinated variants of protective groups that are in common use in oligosaccharide synthesis.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2001
National Category
Chemical Sciences
Identifiers
urn:nbn:se:umu:diva-4378 (URN)10.1021/ol015759+ (DOI)
Available from: 2005-01-28 Created: 2005-01-28 Last updated: 2017-12-14Bibliographically approved
3. A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides
Open this publication in new window or tab >>A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides
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2004 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 6, no 26, 4885-4888 p.Article in journal (Refereed) Published
Abstract [en]

A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2004
National Category
Chemical Sciences
Identifiers
urn:nbn:se:umu:diva-14080 (URN)10.1021/ol048053z (DOI)
Available from: 2008-04-18 Created: 2008-04-18 Last updated: 2017-12-14Bibliographically approved
4. Fluorinated Protective Groups for On-Resin Quantification of Solid- Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
Open this publication in new window or tab >>Fluorinated Protective Groups for On-Resin Quantification of Solid- Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
2002 (English)In: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 3, no 12, 1266-1269 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
John Wiley & Sons, 2002
National Category
Chemical Sciences
Identifiers
urn:nbn:se:umu:diva-4380 (URN)10.1002/1439-7633(20021202)3:12<1266::AID-CBIC1266>3.0.CO;2-6 (DOI)
Available from: 2005-01-28 Created: 2005-01-28 Last updated: 2017-12-14Bibliographically approved
5. Solid-Phase Synthesis of α-Gal Epitopes: On-Resin Analysis of Solid-Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
Open this publication in new window or tab >>Solid-Phase Synthesis of α-Gal Epitopes: On-Resin Analysis of Solid-Phase Oligosaccharide Synthesis with 19F NMR Spectroscopy
2003 In: Journal of Organic Chemistry, Vol. 68, 7281-7288 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:umu:diva-4381 (URN)
Available from: 2005-01-28 Created: 2005-01-28Bibliographically approved

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