Convergent Synthesis of Branched β-Glucan Tridecasaccharides Ready for Conjugation

Xin Zhou; Qing Long; Dongwei Li; Jingru Gao; Qikai Sun; Shaozi Sun; Yong Su; Peng Wang; Wenjie Peng; Ming Li

doi:10.1055/a-1440-9386

Synthesis, Table of Contents

Synthesis 2021; 53(14): 2435-2448
DOI: 10.1055/a-1440-9386

paper

Convergent Synthesis of Branched β-Glucan Tridecasaccharides Ready for Conjugation

Xin Zhou

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Qing Long

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Dongwei Li

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Jingru Gao

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Qikai Sun

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Shaozi Sun

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Yong Su

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Peng Wang

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

,

Wenjie Peng∗

^bLaboratory of Systems Biomedicine, Chinese Ministry of Education, Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China

,

Ming Li∗

^aKey Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China

^cLaboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China

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Abstract

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Abstract

Structurally defined and pure oligosaccharides corresponding to β-glucans have attracted great attention because of their potential properties as immunostimulating agents and as antigens of vaccine candidates. We herein describe a convergent synthesis of ready-to-conjugate tridecasaccharides composed of a β-1,3-glucan nonasaccharide backbone and a β-1,6-glucan tetrasaccharide branch. The assembly was achieved by employing trichloroacetimidate glycosylations and features the gram-scale preparation of the nonasaccharide backbone and installation of the tetrasaccharide branch involving orthoester rearrangement to the glycoside.

Key words

β-glucans - glycosyl trichloroacetimidates - oligosaccharide synthesis - orthoester rearrangement - convergent synthesis

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References

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