1. Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative.
- Author
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Zou XP, Qin CJ, Hu J, Fu JJ, Tian GZ, Moscovitz O, Seeberger PH, and Yin J
- Subjects
- Amines chemical synthesis, Gram-Negative Bacteria chemistry, Heptoses chemical synthesis, Lipopolysaccharides chemistry, Organotin Compounds chemical synthesis
- 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., (Copyright © 2020 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.)
- Published
- 2020
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