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Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen
Chunjun Qin1,2, Benjamin Schumann2, Xiaopeng Zou1,2
1Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University , Wuxi, Jiangsu Province 214122, P.R. China.
Abstract:
Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.
Insights
Researchers synthesized a complex trisaccharide from Plesiomonas shigelloides, a bacterium causing severe diarrhea and infections. This work advances the development of vaccines and diagnostics against this growing public health threat.
Area of Science:
- Carbohydrate Chemistry
- Glycobiology
- Medical Microbiology
Background:
- Plesiomonas shigelloides causes severe travelers' diarrhea and life-threatening extraintestinal infections.
- Increasing antibiotic resistance and lack of vaccines necessitate novel approaches for P. shigelloides control.
- Pathogen-specific carbohydrate antigens are crucial targets for vaccine and diagnostic development.
Purpose of the Study:
- To achieve the total synthesis of the trisaccharide repeating unit of Plesiomonas shigelloides serotype 51.
- To establish a synthetic strategy for complex glycans with unique amino group modifications.
Main Methods:
- Total synthesis of a trisaccharide from three distinct monosaccharide building blocks.
- Strategic installation of N-acetyl (Ac), acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups on amino sugars.
- Development of selective amino group differentiation techniques.
Main Results:
- Successfully synthesized the highly functionalized trisaccharide repeating unit of P. shigelloides serotype 51.
- Demonstrated the feasibility of incorporating rare acetamidino and d-3-hydroxybutyryl modifications.
- Established a robust method for differentiating multiple amino groups on sugar residues.
Conclusions:
- The synthetic route provides access to a key P. shigelloides antigen.
- The developed strategy for amino group modification is applicable to other complex glycan syntheses.
- This research contributes to the potential development of P. shigelloides vaccines and diagnostics.
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