- Synthesis of Defined and Functionalized Glycans of Lipoteichoic Acid: A Cell Surface Polysaccharide from Clostridium difficile
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Two structurally defined, functionalized glycans of lipoteichoic acid (LTA, also known as PS-III) from C. difficile, which have one or two repeating units of LTA linked to the core trisaccharide, were efficiently synthesized via a convergent [2 + 3] or [2 + 2 + 3] strategy. The α-linkage of both N-acetylglucosamine residues in the repeating unit were constructed with glycosyl imidates of azidosugars as donors, while the phosphodiester bridges between the oligosaccharides were fashioned using H-phosphonate chemistry. Both synthetic targets contained a 3-aminopropyl group at the core trisaccharide reducing end, facilitating their conjugation to other biomolecules to afford conjugates useful for various biological studies and applications.
- Yu, Kang,Bi, Ningning,Xiong, Chenghe,Cai, Shuihong,Long, Zhongzhu,Guo, Zhongwu,Gu, Guofeng
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p. 3123 - 3126
(2017/06/23)
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- Synthesis and applications of a light-fluorous glycosyl donor
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A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F 17-Silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.
- Zhang, Fa,Zhang, Wei,Zhang, Yan,Curran, Dennis P.,Liu, Gang
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supporting information; experimental part
p. 2594 - 2597
(2009/08/07)
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- Iterative one-pot synthesis of oligosaccharides
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Straight to the point! Preactivation of a p-tolyl thioglycoside donor, followed by sequential addition of p-tolyl thioglycosyl acceptors in one reaction flask allowed rapid syntheses of oligosaccharides independent of anomeric reactivities of donors and a
- Huang, Xuefei,Huang, Lijun,Wang, Haisheng,Ye, Xin-Shan
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p. 5221 - 5224
(2007/10/03)
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- Selective electrochemical glycosylation by reactivity tuning
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Electrochemical glycosylation of a selenoglycoside donor proceeds efficiently in an undivided cell in acetonitrile to yield β-glycosides. Measurement of cyclic voltammograms for a selection of seleno-, thio-, and O-glycosides indicates the dependence of o
- France, Robert R.,Compton, Richard G.,Davis, Benjamin G.,Fairbanks, Antony J.,Rees, Neil V.,Wadhawan, Jay D.
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p. 2195 - 2202
(2007/10/03)
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