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  Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative

Zou, X., Qin, C.-J., Hu, J., Fu, J.-J., Tian, G.-Z., Moscovitz, O., et al. (2020). Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative. Chinese Journal of Natural Medicines, 18(8), 628-632. doi:/10.1016/S1875-5364(20)30075-3.

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 Creators:
Zou, Xiaopeng1, Author              
Qin, Chun-Jun, Author
Hu, Jing, Author
Fu, Jun-Jie, Author
Tian, Guang-Zong, Author
Moscovitz, Oren2, Author              
Seeberger, Peter H.1, Author              
Yin, Jian, Author
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              
2Oren Moscovitz, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_3176803              

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Free keywords: HBP-3--amyl amine, HP-1--amyl amine, 3--Alkylation, NIS-mediated phosphorylation
 Abstract: D-Glycero-D-mannno-heptose 1β, 7-bisphosphate (HBPβ) is an important intermediate for constructing the core structure of Gram-negative bacterial lipopolysaccharides and was reported as a pathogen-associated molecular pattern (PAMP) that regulates immune responses. HBPβ with 3-O-amyl amine linker and its monophosphate derivative D-glycero-D-mannno-heptose 7-phosphate (HP) with 1α-amyl amine linker have been synthesized as candidates for immunity study of HBPβ. The O3-amyl amine linker of heptose was installed by dibutyltin oxide-mediated regioselective alkylation under fine-tuned protecting condition. The stereoselective installation of 1β-phosphate ester was achieved by NIS-mediated phosphorylation at low temperature. The strategy for installation of 3-O-amyl amine linker onto HBP derivative can be expanded to the syntheses of other conjugation-ready carbohydrates bearing anomeric phosphoester.

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Language(s): eng - English
 Dates: 2020-08-042020
 Publication Status: Published in print
 Pages: -
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 Rev. Type: -
 Identifiers: DOI: /10.1016/S1875-5364(20)30075-3
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Title: Chinese Journal of Natural Medicines
Source Genre: Journal
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Publ. Info: Beijing : China Pharmaceutical Univ.
Pages: - Volume / Issue: 18 (8) Sequence Number: - Start / End Page: 628 - 632 Identifier: ISBN: 1875-5364