Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative.
10.1016/S1875-5364(20)30075-3
- Author:
Xiao-Peng ZOU
1
,
2
;
Chun-Jun QIN
3
;
Jing HU
1
,
4
;
Jun-Jie FU
3
;
Guang-Zong TIAN
1
,
2
;
Oren MOSCOVITZ
5
;
Peter H SEEBERGER
5
;
Jian YIN
6
Author Information
1. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China
2. Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam 14476, Germany.
3. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China.
4. Wuxi School of Medicine, Jiangnan University, Wuxi 214122, China.
5. Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam 14476, Germany.
6. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China. Electronic address: jianyin@jiangnan.edu.cn.
- Publication Type:Journal Article
- Keywords:
3-O-Alkylation;
HBPβ-3-O-amyl amine;
HP-1α-O-amyl amine;
NIS-mediated phosphorylation
- From:
Chinese Journal of Natural Medicines (English Ed.)
2020;18(8):628-632
- CountryChina
- Language:English
-
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.
