Total synthesis of D-glycero-D-mannno-heptose 1ß, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative.
Chin J Nat Med
; 18(8): 628-632, 2020 Aug.
Article
in En
| MEDLINE
| ID: mdl-32768170
ABSTRACT
D-Glycero-D-mannno-heptose 1ß, 7-bisphosphate (HBPß) 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. HBPß 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 HBPß. The O3-amyl amine linker of heptose was installed by dibutyltin oxide-mediated regioselective alkylation under fine-tuned protecting condition. The stereoselective installation of 1ß-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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Organotin Compounds
/
Lipopolysaccharides
/
Amines
/
Gram-Negative Bacteria
/
Heptoses
Language:
En
Journal:
Chin J Nat Med
Year:
2020
Document type:
Article
Affiliation country: