PMID: 11929248Apr 4, 2002Paper

Solid-phase synthesis of oligosaccharides and on-resin quantitative monitoring using gated decoupling (13)C NMR

Journal of the American Chemical Society
Takuya KanemitsuOsamu Kanie

Abstract

A general strategy for solid-phase oligosaccharide synthesis capable of nondestructive quantitative monitoring has been developed. The synthesis was carried out on TentaGel using thioglycosides as glycosylating agents and dimethylthiomethylsulfonium triflate as the activator. An acylsulfonamide linker was introduced to cleave the oligosaccharide from the resin. The solid-phase reactions were monitored quantitatively by using the inverse gated decoupling technique of (13)C NMR, where two (13)C-enriched markers were used to monitor the reactions: one was (13)C-enriched glycine incorporated as a part of the linker and as an internal standard, and the other was a (13)C-enriched acetyl group used as a protecting group of the glycosylation reagent. A representative synthesis of sialyl Lewis X branched tetrasaccharide was demonstrated.

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Citations

Dec 5, 2002·Chembiochem : a European Journal of Chemical Biology·Mickael MogemarkJan Kihlberg
Jun 27, 2003·Current Opinion in Chemical Biology·A Jonathan Wills, Shankar Balasubramanian
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Mar 8, 2008·Journal of Mass Spectrometry : JMS·Yuki ShioiriOsamu Kanie
Apr 22, 2017·Journal of Mass Spectrometry : JMS·F M Nachtigall, L S Santos
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May 19, 2007·Journal of Mass Spectrometry : JMS·Shusaku DaikokuOsamu Kanie
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Oct 26, 2016·ChemistryOpen·Rituparna Das, Balaram Mukhopadhyay
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May 13, 2003·Journal of Combinatorial Chemistry·Jae Wook LeeYoung-Tae Chang
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Sep 25, 2004·The Journal of Organic Chemistry·Sultan N BaytasRobert J Linhardt
Oct 24, 2002·Journal of the American Chemical Society·Shino Manabe, Yukishige Ito

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