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Synthesis 2024; 56(19): 3009-3018
DOI: 10.1055/a-2341-3462
paper

Chemical Synthesis of a Disaccharide from Vibrio vulnificus Biotype 2 Serovar A O-Antigen Containing a Rare l-GalpNAmA

Shengyong Zhu
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
b   Affiliated Children’s Hospital of Jiangnan University, Wuxi 214023, P. R. of China
,
Jing Hu
c   Wuxi School of Medicine, Jiangnan University, Wuxi 214122, P. R. of China
,
Qingjun You
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
b   Affiliated Children’s Hospital of Jiangnan University, Wuxi 214023, P. R. of China
c   Wuxi School of Medicine, Jiangnan University, Wuxi 214122, P. R. of China
,
Guangzong Tian
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
,
Xiaopeng Zou
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
,
Chunjun Qin∗
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
,
Jian Yin
a   Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, P. R. of China
d   School of Life Sciences and Health Engineering, Jiangnan University, Wuxi 214122, P. R. of China
› Author AffiliationsThe authors are grateful to the National Key R&D Program of China (No. 2023YFC2308000), the National Natural Science Foundation of China (22325803, 22277042, 22077052, 22177041), and the Project of Taihu Talent Plan.
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Abstract

The bacterium Vibrio vulnificus can cause severe infections internally and externally. The mortality rate of V. vulnificus-associated gangrene and septicemia has increased due to antibiotic resistance and the absence of human vaccine. Bacterial carbohydrates have been widely used in the development of bacterial vaccines. Here, a rare l-GalpNAmA-containing disaccharide that exists in V. vulnificus biotype 2 serovar A O-antigen was synthesized from d-glucose and l-galactose. An investigation on the influence of different linkers on the disaccharide synthetic efficiency indicated that the amine linker has more practicality. Two α-glycosidic linkages were constructed with good stereoselectivity by using nonparticipating C2 azido group and solvent effect. An orthogonal protection strategy allowed introductions of carboxyl and acetamidino (Am) groups at the disaccharide stage. The synthesis of the amine-linked disaccharide will provide a basis for the preparation of the trisaccharide repeating unit and longer fragments of V. vulnificus biotype 2 serovar A O-antigen, as well as other complex glycans.

Key words

Vibrio vulnificus - O-antigen - oligosaccharide - chemical synthesis - C6 oxidation - acetamidino group

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2341-3462.
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Publication History

Received: 14 April 2024

Accepted after revision: 07 June 2024

Accepted Manuscript online:
07 June 2024

Article published online:
27 June 2024

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