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

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.

journal_name

Chin J Nat Med

authors

Zou XP,Qin CJ,Hu J,Fu JJ,Tian GZ,Moscovitz O,Seeberger PH,Yin J

doi

10.1016/S1875-5364(20)30075-3

subject

Has Abstract

pub_date

2020-08-01 00:00:00

pages

628-632

issue

8

eissn

2095-6975

issn

1875-5364

pii

S1875-5364(20)30075-3

journal_volume

18

pub_type

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