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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
a   Key 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
a   Key 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
a   Key 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
a   Key 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
a   Key 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
a   Key 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
a   Key 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
a   Key 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∗
b   Laboratory of Systems Biomedicine, Chinese Ministry of Education, Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Ming Li∗
a   Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. of China
c   Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, P. R. of China
› Author AffiliationsWe are grateful for financial support from the National Natural Science­ Foundation of China (Nos. 21672194 and 21977088), the National­ Natural Science Foundation of China-Shandong Joint Fund (No. U1906213), and the Natural Science Foundation of Shandong Province (No. ZR2018MB015).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1440-9386.
  • Supporting Information


Publication History

Received: 19 February 2021

Accepted after revision: 16 March 2021

Accepted Manuscript online:
16 March 2021

Article published online:
12 April 2021

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