Organic Letters
Organic Letters
5 years ago

Synthesis of Defined and Functionalized Glycans of Lipoteichoic Acid: A Cell Surface Polysaccharide from Clostridium difficile

Synthesis of Defined and Functionalized Glycans of Lipoteichoic Acid: A Cell Surface Polysaccharide from Clostridium difficile
Kang Yu, Shuihong Cai, Zhongzhu Long, Chenghe Xiong, Guofeng Gu, Ningning Bi, Zhongwu Guo
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01242

DOI: 10.1021/acs.orglett.7b01242

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