Rapid identification of common hexapyranose monosaccharide units by a simple TOCSY matching approach

Chemistry : a European Journal
Katelijne GheysenJosé C Martins

Abstract

Solution NMR spectroscopy is a well established technique for non-destructive characterization of the structures and conformations of complex oligo- and polysaccharides. One of the key experiments involves the use of 2D TOCSY to collect the 1H spins into groups that can be associated with the individual saccharide units that are present in the molecule under study. It is well known that the magnetization transfer rate through the 1H spin system during the TOCSY spin lock period is sensitive to the intervening 3J(H,H) scalar couplings, and therefore also to the saccharide stereochemistry. Here, we have investigated the potential to extract information on the stereochemistry of hexapyranose monosaccharide units directly from TOCSY spectra. Through a systematic experimental investigation of the magnetization transfer initiated from the anomeric 1H resonance in D-glucose, D-galactose and D-mannose it is shown that a 100 ms spin lock time provides optimal spectroscopic discrimination between these three commonly occurring building blocks. A simple matching scheme is proposed as a new tool for rapid attribution of the TOCSY traces originating from the anomeric 1H resonances towards the underlying monosaccharide type. The scheme appea...Continue Reading

References

Mar 11, 1992·Nucleic Acids Research·C WijmengaR R Frants
May 15, 1988·Analytical Biochemistry·N TomiyaN Takahashi
Mar 1, 1987·Proceedings of the National Academy of Sciences of the United States of America·S W HomansT W Rademacher
Jun 15, 1995·European Journal of Biochemistry·H OgawaI Matsumoto
Aug 10, 2005·Journal of Pharmaceutical and Biomedical Analysis·Christopher Jones

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Citations

Jun 21, 2012·The Journal of Organic Chemistry·Justyna SikorskaKerry L McPhail
May 7, 2011·World Journal of Gastroenterology : WJG·Jian WangJian-Ping Lu
Oct 21, 2016·Journal of Magnetic Resonance·Neil MacKinnonJan G Korvink
Oct 28, 2016·Biotechnology and Bioengineering·Inge N A Van BogaertWim K Soetaert
Dec 18, 2014·Journal of Natural Products·Silvia C Heredia-VieiraFrancisco A Macías
May 7, 2020·Biotechnology and Bioengineering·Bram LaukensNico Callewaert
Feb 26, 2019·The Journal of Experimental Medicine·Peter ReininkIldiko Van Rhijn
Jun 12, 2019·Proceedings of the National Academy of Sciences of the United States of America·Matthew T HenkeJon Clardy
Aug 2, 2014·Organic Letters·Tadeusz F Molinski
Jul 18, 2014·The Journal of Organic Chemistry·Mattie S M TimmerBridget L Stocker

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