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Expedient Synthesis of the Cap Tetrasaccharide of Leishmania Lipophosphoglycan

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2026

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Lv, Jianwu
Gou, Lihong
Li, Tianlu

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https://doi.org/10.1002/ejoc.202501052
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National Natural Science Foundation of China: 92478125
National Natural Science Foundation of China: 22577062
National Natural Science Foundation of China: 22177061

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Chemie: Publikationen
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European Journal of Organic Chemistry. Wiley. 2026, 29(6), e202501052. ISSN 1434-193X. eISSN 1099-0690. Verfügbar unter: doi: 10.1002/ejoc.202501052

Zusammenfassung

Leishmaniasis remains an ignored tropical disease with urgent need for safe and effective vaccines. The lipophosphoglycans (LPGs) of Leishmania parasites is a key virulence factor, and its terminal cap tetrasaccharide represents a structurally conserved antigen suitable for vaccine development. Herein, we report a concise and practical route to synthesize the cap tetrasaccharide. This synthesis strategy highlights (i) regioselective axial benzoylation of mannosyl units via the “cyanide effect,” providing quick and orthogonally protected building blocks in large scale, and (ii) highly stereoselective glycosidation under AuCl3–tBuCN cooperative catalysis, which ensures efficient formation of challenging β-(1,4)-galactosidic linkages without neighboring participation. These protocols are operationally simple, minimize protecting group manipulations, and are highly reproducible, thus enabling in-depth biological studies and translational implementation.

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540 Chemie

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ISO 690LV, Jianwu, Lihong GOU, Richard R. SCHMIDT, Peng PENG, Tianlu LI, 2026. Expedient Synthesis of the Cap Tetrasaccharide of Leishmania Lipophosphoglycan. In: European Journal of Organic Chemistry. Wiley. 2026, 29(6), e202501052. ISSN 1434-193X. eISSN 1099-0690. Verfügbar unter: doi: 10.1002/ejoc.202501052
BibTex
@article{Lv2026-02-13Exped-75766,
  title={Expedient Synthesis of the Cap Tetrasaccharide of Leishmania Lipophosphoglycan},
  year={2026},
  doi={10.1002/ejoc.202501052},
  number={6},
  volume={29},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  author={Lv, Jianwu and Gou, Lihong and Schmidt, Richard R. and Peng, Peng and Li, Tianlu},
  note={Article Number: e202501052}
}
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